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Author: Subject: What to do with this compound?
LiD
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[*] posted on 28-8-2013 at 16:03
What to do with this compound?


I have just got a larger amount of this:

But I have idea, that what could be made of it or how could I use it. I thought a reaction similar that is described here: http://pubs.rsc.org/en/Content/ArticleLanding/1990/P1/p19900...

Any ideas?
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bfesser
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Paddywhacker
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[*] posted on 28-8-2013 at 19:16


Looks like a good hydrogen donor for homogenous hydrogenations.
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kavu
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[*] posted on 28-8-2013 at 22:04


Mostly the compound is synthetically useful when deprotonated and used as a nucleophile. However you can hydrolyze the stuff to 1,3-cyclohexanedione using aq. HCl:

"Crude 5 (1 equiv.) was dissolved in acetone (5 mL/mmol) and aq. 2N HCl (3 equiv.) added. The resulting solution was stirred overnight at r.t. The acetone was evaporated under reduced pressure and the residue diluted (H2O), basified (aq. 1N NaOH)andwashed with Et2O. The aqueous layer was reacidified (pH 1–3 aq. 2N HCl) and extracted with EtOAc. The organic phase was dried (MgSO4) and concentrated in vacuo to return 1 as a white solid." Org. Biomol. Chem., 2009,7, 4296-4300
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Nicodem
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AndersHoveland
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[*] posted on 10-9-2013 at 18:03


When ethyl acetate is treated with alcoholic ammonia, it gives acetamide. Does anyone know if this would work on aryl esters? (could one get 1,3-diaminobenzene?)
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FreeMirage
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[*] posted on 30-9-2013 at 05:16


Acetamide is an amide, the electron withdrawing effects of the carbonyl allow the hydroxyl to be very reactive, this compound on the other hand is an aryl ether and those bonds are much harder to break. I doubt alcoholic ammonia would do much here.
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palico
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[*] posted on 1-10-2013 at 09:41


I would try to demethylate obtaining the diol and then make the polymer with terephtalic acid.
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