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garryb
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[*] posted on 19-1-2007 at 07:34
Names of dicarboxylic acids


For many years now I have been collecting the trivial names of straight chain alpha,omega-dicarboxylic acids.
Those I am aware of are as follows for COOH(CH2)nCOOH.
Where n = 0 Oxalic acid
1 Malonic
2 Succinic
3 Glutaric
4 Adipic
5 Pimelic
6 Suberic
7 Azelaic
8 Sebacic

Can anyone extend this series for me?
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[*] posted on 19-1-2007 at 07:35


I apologise for posting that in biochemistry - perhaps organic chemistry would have been better.
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[*] posted on 19-1-2007 at 19:38


I don't think that the trival names go any further than your list, I don't remember seeing any although there could be some.

The last 2 or 3 on the list were considered difficult to obtain, and this expensive, because their production from natural materials gave very low yields. There aren't many reasonably common natural materials that have reactive groups in the correct location to for the dicarboxylic acids.

Telomersation reactions give a simple path to longer chain diacids, but generally as a mixture that is difficult to process into the pure, isolated compounds. And as this is a purely synthetic route, starting with ethylene and a poly-halo methan or ethane, trival names didn't come up.
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[*] posted on 19-1-2007 at 20:13


The dicarboxylic acids can be extended by two carbon atoms at a time:
For example, succinic acid (n=2) is reduced to 1,4- butanediol with e.g. LiAlH4 or Na in ethanol, or catalytic hydrogenation (I know that 1,4-B is a large- scale industrial product and synthesis would be uneconomic, but it is just an example) and esterified with HBr to 1,4- dibromobutane.
This is then reacted with 2 mol sodium cyanide to obtain 1,4- dicyanobutane (adiponitrile), and upon hydrolysis with acid or base, adipic acid (n=4) is obtained (this is actually an industrial route to adipic acid, since 1,4-B and NaCN are very cheap high- volume industrial products).

This process could then be repeated with adipic acid to yield suberic acid, and so on.

That way, dicarboxylic acids with every number of carbon atoms can be obtained by starting with either one where n is divisable by two, or with one where n is not divisable by two.




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[*] posted on 20-1-2007 at 00:05


I am very sure that there are quite a few members who are slavering for specific procedures to reduce succinic acid to BDO or succinic anhydride to GBL on a bench scale.

Others probably know them already.
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[*] posted on 12-2-2007 at 22:28


The trivial names do go farther.. see Wikepedia for a longer list: http://en.wikipedia.org/wiki/Dicarboxylic_acid
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[*] posted on 13-2-2007 at 00:09


Quote:
Originally posted by chemrox
The trivial names do go farther.. see Wikepedia for a longer list: http://en.wikipedia.org/wiki/Dicarboxylic_acid


Looks to be identical with the list in garryb's original post, which is for the "straight chain alpha,omega-dicarboxylic acids". Wiki also include phthalic acid, which is aromatic rather than staight chain aliphatic.
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[*] posted on 13-2-2007 at 10:12


Thanks for all the input people. I must say I think not_important's post is more accurate than chemrox's, but all posts have been appreciated. I confess to a liking for the old trivial names in organic chemistry, although of course I appreciate the "unambiguousness" and "systematic-ness" of newer nomenclature. I had hoped that names beyond sebacic might exist, but it appears not. Thanks again everyone.
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[*] posted on 13-2-2007 at 10:37


Speaking of carboxylic acids, what is (if it exists) C(COOH)4?

Tim




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[*] posted on 13-2-2007 at 11:35


Quote:
Originally posted by 12AX7
Speaking of carboxylic acids, what is (if it exists) C(COOH)4?

Tim


It's what you'd get by oxidising pentaerythritol. I don;t think it would be very stable, replace two CO2H with H and you've got malonic acid, I'd expect the tetra-carboxylic version to decarboxylate much more readily.

You might be able to sneak up on it through routes that would make an tetra-ester of the acid. I can't seem to find any reference of the acid or simple derivtives except for http://www.springerlink.com/content/k8884t6811962415/
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[*] posted on 24-2-2007 at 22:36


This was right to begin with. The numbering threw me:

1 Malonic
2 Succinic
3 Glutaric
4 Adipic
5 Pimelic
6 Suberic
7 Azelaic
8 Sebacic

versus:

acid alkane
oxalic ethane
Malonic propane
Succinic butane
Glutaric pentane
Adipic hexane
Pimelic heptane
Suberic octane
Azelaic nonane
Sebacic decane

sorry for my confusion
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[*] posted on 24-2-2007 at 22:50


chemrox's posting reminded me that I had found several more entries in one of my old ochem books.

Brassylic acid HOOC(CH2)11COOH

Thapsic acid HOOC(CH2)14COOH


And a couple of unsaturated ones

Traumatic acid (10E-dodeca-1,12-dicarboxylic acid)



Crocetin A C20 polyunsaturated dicarboxylic
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[*] posted on 28-2-2007 at 17:07


Quote:
Originally posted by 12AX7
Speaking of carboxylic acids, what is (if it exists) C(COOH)4?
Tim

That would be called neopentane-tetracarboxylic acid, or pentaerythro-tetracarboxylic acid. Under milder conditions than that for decarboxylation, it would have a marked tendency to dehydrate to a polymeric anhydride.
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[*] posted on 3-3-2007 at 10:06


Quote:
Originally posted by 12AX7
Speaking of carboxylic acids, what is (if it exists) C(COOH)4?

Tim

Interesting question. Though methanetetracarboxylic acid as such can not exist due to obvious reasons, its salts, esters and amides do exist. Here are the references for their preparation:

Sodium methanetetracarboxylate from pentaerythritol.
JP52128317
Abstract: Pd-catalyzed oxidn. of 2% to satd. aq. C(CH2OH)4 with O at 40-120°C; and pH 7-13 with addn. of NaOH gave C(CO2Na)4. Thus, 125 L/h O was introduced into 800 g 7.5% aq. C(CH2OH)4 contg. 2.4 g 5% Pd-C at 59-61°C; for 150 min while keeping the pH at 10.0  0.1 with NaOH, and the soln. was clarified and evapd. The residue contained 80% C(CO2Na)4.


Methanetetracarboxylic esters.
Backer, H. J.; Lolkema, J.
Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1939), 58 23-33.
Abstract: cf. C. A. 33, 1669.5. The methanetetracarboxylic esters (I) show the properties of "compacted mols." The Me and iso-Pr esters, compact and sym. groups, are cryst. whereas the mixed esters are liquid. In comparison with the esters of methanetetraacetic acid, those of I are more "compact," with higher m. p. and less limited liquidity intervals. I are prepd. by acting on the Na deriv. of methanetricarboxylates with an excess of chloroformates. A mixt. of 50.8 g. (0.2 mol.) of NaC(CO2Et)3 with 108 g. (1 mol.) of ClCO2Et was heated at 100-5°C; for 4 hrs. with continued stirring, yielding 49 g. (80%) of C(CO2Et)4 (II), m. 12-13°C;, b2.5 146-7°C;, nD20 1.4309. Similarly were prepd. the methanetetracarboxylates: Me, m. 74-5°C; (C. A. 7, 2208); Pr, b12 200°C;, nD20 1.4387; iso-Pr, m. 76°C;, b12-13 176°C;, in 41% yields of rhombic crystals; Bu, b1.5 184-5°C;, nD20 1.4427, in 61% yields. Since the addn. of iso-BuONa to (iso-BuO2C)3CH does not ppt. the Na deriv. it was prepd. by heating a suspension of 2.3 g. Na in 80 cc. of xylene with 31.6 g. of (iso-BuO2C)3-CH in 30 cc. of xylene for 1 hr. After the addn. of 22 g. of iso-BuO2CCl the mixt. was heated for 3 hrs. at 135°C;, yielding, on working up, 15.8 g. (38%) of iso-Bu methanetetracarboxylate, b3 177-8°C;, nD20 1.4397. The following methanetetracarboxylates were similarly prepd.: sec-Bu, m. 42-3°C;, b2.5 173-4°C;, in 51% yields; Am, b2.5 215.0-15.5°C;, nD20 1.4449 (65%); iso-Am, b4-5 214-17°C; nD20 1.4442(48%); sec-Am, b0.0002 134-5°C;, b2.5 184°C;, nD20 1.4457 (24%); decyl, b0.001 240-1°C; nD20 1.4552; cyclohexyl, m. 110°C;, in 3.3% yields of rhombic crystals. The following mixed esters were prepd. by heating mixts. of the appropriate Na deriv. of the appropriate methanetricarboxylic ester with excess of a suitable chloroformic ester: di-Me diiso-Pr, C13H20O8, m. -5°C; b2.5, 141°C;, nD20 1.4313 (61% yield); Me triiso-Pr, C15H24O8, b2.5 140-1°C; nD20 1.4292 (27%); triiso-Pr sec Bu, C18H30O8, m. 35-6°C;, b5 167-8°C;; triiso-Pr cyclohexyl, C20H32O8, b2.5 172-3°C;, nD20 1.4547; triiso-Pr Ph, C20H26O8, m. 73.5-4.0°C;, in 46% yields of triclinic crystals; triiso-Pr p-tolyl, C21H28O8, m. 62-3°C;. Refluxing a mixt. of 7 g. Na, 15 g. CO(NH2)2 and 30 g. II in 300 cc. abs. alc. for 7 hrs. yielded barbituric acid, m. 250-1°C; (decompn.). Heating 10 g. II with 31 g. PhNH2 gave 5 g. of malonanilide, m. 229-30°C;, and 10 g. of carbanilide, m. 240-1°C;. Thus under the influence of CO(NH2)2 and PhNH2, II loses 2 CO2Et groups and forms CH2(CO2H)2 derivs. Loss of symmetry of the mol. by introduction of a different group lowers the m. p. and complicates the crystallographic system.

Ring closure in polycarboxylic acids. II. Course of the amidation in ethanetetracarboxylic, ethanehexacarboxylic, methanetri- and methanetetracarboxylic esters.
Philippi, Ernst; Hanusch, Jilie; von Wacek, Anton.
Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1921), 54B 895-902.
Abstract: cf. C. A. 14, 3672. When 12 cc. dry liquid NH3 and 10 g. [CH(CO2Et)2]2 cooled with CO2-Me2CO are sealed in a tube and allowed to stand 3 days, there sep. long transparent crystals which over H2SO4 soon become turbid and opaque and lose NH3, falling to a white powder. The freshly prepd. crystals yield on analysis values corresponding to those for [CH(CONH2)2]2 and the powder resulting from its decompn. over H2SO2 is 2,5-diketopyrrolidine-3,4-dicarboxamide; this, heated in vacuo in a slow current of dry air at 200°C;, loses another mol. of NH3 and gives 30% of ethanetetracarboxylic diimide (2,5-diketopyrrolidine-3,4-dicarboximide). A repetition of Mulliken's work (Am. Chem J. 15, 527(1893)) confirmed his observation that [C(CO2Et)3]2 can be prepd. only by electrosynthesis; by the following modification of his method, the yield was increased to 20%: 15 g. NaC(CO2Et)3 in 30 cc. H2O are electrolyzed in a Pt crucible (cathode) with a Pt spiral anode and an av. current of 4 amp. at 9 v. for about 1.5 hrs., then neutralized with dil. H2SO4, extd. with Et2O, freed from CH2(CO2Et)2 and CH(CO2Et)3 in vacuo and crystd. from Et2O; attempts to amidate it either as above with liquid NH3 or with alc. NH3 up to 150°C; yielded only the unchanged ester. CH(CO2Et)2 was prepd. by the method of Scholl and Egerer (C. A. 7, 2208) but by prolonging the heating the yield was increased to 80%. When allowed to stand 3 days with liquid NH3 it yielded CH2(CONH2)2 and H2NCO2Et almost quant. C(CO2Et)4 (8 g. from 20 g. NaC(CO2Et)3 by S. and E.'s method) behaved similarly on amidation.
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[*] posted on 3-3-2007 at 10:57


Hmm interesting :)



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[*] posted on 6-7-2008 at 11:35


Quote:
Originally posted by Sauron
I am very sure that there are quite a few members who are slavering for specific procedures to reduce succinic acid to BDO or succinic anhydride to GBL on a bench scale.

Others probably know them already.


While thinking about GHB syntheses today, the following scheme came to mind:

1. React succinic anhydride with an alkanol (methyl, ethyl) to get to alkyl hydrogen succinate.

2. Reduce the ester group with NaBH4 in THF/MeOH.

3. Isolate & purify your GHB, probably as a salt. I believe I've read that the Ca salt is non-hygroscopic.

I can't claim that this is an original approach, but the first step is Organic 101 & I've just checked references that discuss using NaBH4 to reduce esters to primary alcohols. I've never worked with this molecule & have no idea how difficult it would be to isolate in a pure form.

As an added thought, if you started this using maleic anhydride instead you'd wind up with the more potent trans-4-hydroxycrotonic acid. The intermediate would be the alkyl hydrogen maleate.

This same synthesis scheme looks to be suitable for preparing the cyclopropane analog of GHB described in the GHB analog thread in the Organic Chemistry forum. In this case the starting anhydride would be the known 3-oxabicyclo[3.1.0]hexane-2,4-dione and the intermediate would be alkyl hydrogen 1,2-cyclopropanedicarboxylate. The reduced form would be a mixture of diasteriomers. One of these (R,R) was described as being the most potent GHB analog.

[Edited on 6-7-2008 by Ritter]




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[*] posted on 7-7-2008 at 01:32


I'd have thought you were capable of recognizing sarcasm when it stares out from the page.



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[*] posted on 7-7-2008 at 04:03


Some people just cannot see further than the drug :D

GBL is readily available by mail order throughout most of Europe as a cleaner. Some companys will post worldwide or just get a mate to pick you some up next time they pass through the UK.
99.9% pure and convertible into Na GBH in a trice in quantitative yield if you gag at drinking industrial cleaner.

So why mess around with wacky multistage syntheses and risk poisoning yourself with byproducts? :(
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[*] posted on 7-7-2008 at 06:11


I long for the days when it was just a lactone and BDO was just a glycol and GHB was a health food supplement. The age of innocence.



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[*] posted on 7-7-2008 at 06:47


The strange thing is that it is such a pathetic drug.

Nice Pimms and ginger ale, watch the sun go down on a summer evening.


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[*] posted on 7-7-2008 at 07:40


Quote:
Originally posted by Ritter
While thinking about GHB syntheses today, the following scheme came to mind:

1. React succinic anhydride with an alkanol (methyl, ethyl) to get to alkyl hydrogen succinate.

2. Reduce the ester group with NaBH4 in THF/MeOH.

3. Isolate & purify your GHB, probably as a salt. I believe I've read that the Ca salt is non-hygroscopic.

I don't know any method for selectively reducing the ester group over the carboxylic one (or vice versa) that uses NaBH4, though probably it exists, but NaBH4 in THF and/or methanol does not reduce either esters nor carboxylic acids. Reduction of aldehydes, ketones and imines is more or less all for what such a system (NaBH4/MeOH) is useful for.
Quote:
As an added thought, if you started this using maleic anhydride instead you'd wind up with the more potent trans-4-hydroxycrotonic acid. The intermediate would be the alkyl hydrogen maleate.

Maleic anhydride gives monomethyl maleate with methanol (that is cis conformation) and the selective reduction of the ester group (or carboxylic group) would give you the cis-4-hydroxy-but-2-enoic acid.




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[*] posted on 7-7-2008 at 11:23


Quote:
Originally posted by Nicodem
Quote:
Originally posted by Ritter
While thinking about GHB syntheses today, the following scheme came to mind:

1. React succinic anhydride with an alkanol (methyl, ethyl) to get to alkyl hydrogen succinate.

2. Reduce the ester group with NaBH4 in THF/MeOH.

3. Isolate & purify your GHB, probably as a salt. I believe I've read that the Ca salt is non-hygroscopic.

Quote:
I don't know any method for selectively reducing the ester group over the carboxylic one (or vice versa) that uses NaBH4, though probably it exists, but NaBH4 in THF and/or methanol does not reduce either esters nor carboxylic acids.


See http://www.springerlink.com/content/0678qn6571725r53/ for one reference to the NaBH4 reduction of esters to primary alcohols. And http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2004/6/i22/a... as well as the links here http://gaussling.wordpress.com/2007/04/07/nabh4-reduction-of....

In March's Advanced Organic Chemistry (5th edition) on page 1546 in Table 19.5 there are 2 footnotes for the conversion of an alkyl ester to a primary alcohol with NaBH4: B (Ref. 496) employs NaBH4 with LiCl; C (Ref. 506) employs NaBH4 with AlCl3. I haven't had time to find URLs for these but here they are:

Ref. 496:

Brown, H.C. Tetrahedron, 1979, 35, 567
Walker, E.R.H. Chem. Soc. Rev. 1976, 5, 23
Brown, H.C. Boranes in Organic Chemistry 1972, p. 209
Additional cited references from Ref. 495:

Rerick, M.N. in Augustine, R.I. Reduction 1968

Ref. 506:

Brown, H.C. et al J Am Chem Soc 1970, 92, 7161

So there is precedent. And the hydride reduction of an ester will be a lot more facile than reduction of a COOH group. It would be interesting to experiment in order to optimize the ester reduction. The only conditions given in March (albeit dated) are that it takes either borane or LAH to reduce COOH groups.

Reduction of aldehydes, ketones and imines is more or less all for what such a system (NaBH4/MeOH) is useful for.
Quote:
As an added thought, if you started this using maleic anhydride instead you'd wind up with the more potent trans-4-hydroxycrotonic acid. The intermediate would be the alkyl hydrogen maleate.

Maleic anhydride gives monomethyl maleate with methanol (that is cis conformation) and the selective reduction of the ester group (or carboxylic group) would give you the cis-4-hydroxy-but-2-enoic acid.


You are correct. I would need monomethyl hydrogen fumarate to get the correct (active) trans isomer.

[Edited on 7-7-2008 by Ritter]

[Edited on 7-7-2008 by Ritter]




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[*] posted on 8-7-2008 at 03:28


The references you provided claim no selectivity of ester vs. carboxylic groups. And the first references actually demonstrates what I already said about the NaBH4/MeOH system – that it can not be used to reduce esters (or carboxylic acids) in any preparative way.
There are numerous methods employing NaBH4 for the reduction of esters, but most of them are based on in situ formation of borane which however does not discriminate between the ester or carboxylic group (though I’m not sure - the reactivity of the both could actually differ enough for preparative use if optimized). This way, borane is made in situ by either reacting NaBH4 with an acid (BF3, AlCl3, ZrCl4, CF3COOH, Me3SiCl, etc.), partial oxidation (with I2) or thermolyticaly (by heating in refluxing diglyme). Some carboxylic groups enabling neighboring group assistance can be reduced directly with NaBH4 even without borane intermediacy (for example alpha-aminoacids). The Organic letters paper you linked uses a similar strategy by artificially forming a micellar ambient where such assistance is offered by the micelle’s surface. However the paper claims no chemoselectivity of the ester over the carboxylic group (carboxylate salts are too polar to enter the hydrophobic micelles anyway). Nevertheless, I uploaded the full paper as it might be of interest to some members (who would want to waste NaBH4 for making something as cheap, available or easily preparable by other means as 4-hydroxybutyric acid anyway?):

Efficient and Simple NaBH4 Reduction of Esters at Cationic Micellar Surface
Debapratim Das, Sangita Roy, and Prasanta Kumar Das
Org. Lett., 6 (2004) 4133 -4136. DOI: 10.1021/ol0481176

Attachment: Efficient and Simple NaBH4 Reduction of Esters at Cationic Micellar Surface.pdf (61kB)
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[*] posted on 29-9-2008 at 18:13


Oh My Such A Good Apple Pie: Classical mnemonic device.
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[*] posted on 1-3-2009 at 01:15


Yeah, OMSGAPSAS ... it works for me.

Azelaic acid should be obtainable from the oxidation of oleic acid by something that cleaves the double bond. Maybe permanganate.

Make the calcium or barium salt and pyrolyse it to give cyclooctanone.
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