any otc galic acid?

[fnord]

any otc galic acid?

[Rhodium]

Various plant matter contains tannins, which essentially consist of a sugar molecule with a few gallic acid molecules attached to it. Extraction of those tannins followed by hydrolysis will give crude gallic acid.

If you google for a few minutes, you can find loads of procedures for these steps as well as suitable plant sources. Take your pick. One example is this (using a rather odd source, but you'll get the point):

http://www.fpl.fs.fed.us/documnts/PDF1997/galve97a.pdf

[Vitus_Verdegast]

Pure tannic acid can easily be obtained from homebrew supply stores, as it is frequently used to clarify wine and beer.

[gsus]

tara pod powder is not so exotic on this side of the atlantic. froogle can't find much, but its there. $1060 for 21 metric tons. wow. tanning is as rewarding a hobby as brewing.

  yes, the hydrolysis is well known, but i just wanted to mention a patent, since Mountain_Girl brought it up before but the # was transposed and never fixed. this alleges higher yields than the hydrolysis above, but uses a lot of solvent. obviously this can be recycled if in fact such large amounts are necessary. hydrolyses with acid, base, tara, nutgalls, and sumac are described in

Patent US2723992

  i'm guessing that the gallic acid might be destined for methylation, so let me ask some questions here of the Hive. would a Deutsch speaking bee care to translate Herzig, Ber. 38, 989 (1905) where tannin was methylated with diazomethane, then hydrolyzed to trimethylgallic acid? if not, then how about the original amphetamine synthesis (for the hell of it) Edeleano, Ber. 20, 616 (1887)? yeah i know there are a lot of more worthy articles to translate, but the Edeleano one sure is historic. and long!

  any comments on one-pot methylation and hydrolysis of gallotannin to the acid or ester?

[ning]

Just exhaustively methylate that sucker, then see

Post 501059

(ning: "TRANSLATED: Chinese 3,4,5 TMB article", Methods Discourse) for conversion to the aldehyde.

BTW, ning doesn't know if this has been done at the hive already, but you can knovenagel condense 3,4,5-TMB with acetonitrile as well as nitromethane. If the double-bond is reduced, then a hoffmann rearrangement will nicely yield a phenethylamine. Refs if desired.

Ning would die to see 10 metric tons of mescaline. Now THAT's large-scale!

[Aurelius]

Ning, somebody like you should know by now that refs are ALWAYS in order for something of interest such as this.

(particularly in the ways of PEA synths)