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Vogelzang
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Here's the schematics from the 1310, 1320, 1330 instruction manual. You can see that it has a lot of digital electronics in it.
Attachment: PE1310-Fig7-1-6.pdf (952kB)
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benzylchloride1
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I have been experimenting with the bromination of 1,2-methylenedioxybenzene in methanol using using sodium bromide, ammonium persulfate and a small
quantity of sulfuric acid, initial yields look to be good. I am planning on doing something quite interesting reguarding the synthesis os sesamol. I
plan to convert the bromo compound into a Grignard reagent and react it with a borate ester and hydrolyze to form the aryl boronic acid. The boronic
acid can then be oxidized with hydrogen peroxide to form sesamol. I am planning on prparing isopropyl borate since methyl borate boiling point is to
close to that of methanol to make separation feasible. Vogel describes a preparation of butyl borate, but I do not have any 1-butanol. Propy borate is
a possibility since 1-propanol can be distilled from some chimney creosote remover sprays that contain it along with manganese (II) nitrate.
Amateur NMR spectroscopist
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Vogelzang
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You might be interested in this article.
Attachment: Labdev1970-p217-218.pdf (197kB)
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Arrhenius
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Forming the aryl boronic acid in high yield may prove trickier than in sounds. Your triisopropyl borate (most preferable) must be dry and free of
alcohols (preferably distilled from Naº). Also, the order of addition and temperature are important, or you'll get diphenylborinic acid, etc. Aryl
boronic acids are often nice crystalline solids, but they can be a pain to purify or characterize due to an equilibrium with the 'anhydride'
dimer/trimer. Other than that, it sounds like a good idea  Though I believe
there are reliable copper(I) catalyzed reactions to go from the aryl halide to the phenol.
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benzylchloride1
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I have been gradually working on the carpanone synthesis, but grad school has slowed down my progress. I had to rethink my initial strategy to produce
sesamol. I ended up running a Blanc chloromethylation reaction on the 1,3-benzodioxole, and then running a Sommlet reaction to produce the piperonal.
I then ran a Dakin oxidation on the piperonal and subsequently hydrolyzed the resulting formate ester to make the sesamol. I then made allyl bromide
via the procedure in Organic Syntheses using glycerol.I then ran a Williamson ether synthesis and then a Claisen Rearrangement to produce
2-allylsesamol. I attempted to isomerize the 2-allylsesamol using potassium hydroxide in DMSO, but all I recovered was a small amount of the starting
material, I then resorted to using potassium tert-butoxide as in the literature procedure to produce a putative propenyl sesamol which I am working on
trying to confirm as the desired product. The UV-vis spectrum demonstrates a large bathochromic shift when compared to the starting 2-allyl sesamol.
The infrared spectra are fairly similar. I am working on getting my NMR to work, hopefully it will be fully working by summer. I am also working on a
structural degradation of the suspected 2-propenylsesamol to produce the corresponding benzaldehyde which I will make a 2,4-dinitrophenylhydrazone
derivative of for identification. I have not been able to find melting point data for the 2,4-DNP hydrazone of this aldehyde in any of my books or
using Scifinder. I have also ran a test oxidative coupling on the suspected 2-propenylsesamol, but I still need to purify the product. I will make
further updates as I have time to upload my infrared and UV-visible spectra. Hopefully, I will soon have my NMR operational and I will post NMR
spectra as well. I have attached a drawing of the aldehyde that I need derivative information on.
[Edited on 2-1-2012 by benzylchloride1]
Attachment: 2-hydroxyl-4,5-methylenedioxybenzaldehyde.pdf (10kB)
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Amateur NMR spectroscopist
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kavu
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What about Friedel-Crafts acylation of 1,3-benzodioxole with acetyl chloride. Dakin reaction of the ketone should produce the desired phenol. This
method would eliminate the use of the easily oxidised aldehyde. I'll have to take a further look on reaxys once I get back to the uni.
[Edited on 2-1-2012 by kavu]
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