Author: S.G. Mel'Kanoviiskaya
Publication: Zh. Org. Khim. vol.1, p325 (1965)
-- PK
TheCat
Member posted 04-26-99 12:12 AM
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Hey psychokitty, you might also want to check out this thread:
http://hive.lycaeum.org/ubb_board/Forum1/HTML/001756.html (http://hive.lycaeum.org/ubb_board/Forum1/HTML/001756.html)
I think its kind of along the same lines.
Peace
TheCat
Rhenium
Member posted 04-26-99 12:24 AM
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Psychokitty : Long time no post my feline friend. I can get the english translation of this (Russian) journal, probably not for a day or two, but I can dig it up.
Rhenium
Rhodium
Administrator posted 04-26-99 06:28 PM
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Speaking of catechol, why have I never seen any formylation/methylenation of this to give piperonal?
Would a vilsmeyer yield the 2,3-substituted benzaldehyde instead (seems strange, as a bromination puts the halogen right on the spot).
If it works, piperonal is only a few hours away from catechol.
psychokitty
Member posted 04-26-99 07:06 PM
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Well, it seems now everbee is putting on his/her thinking cap. Fuck safrole. It's soon to be obsolete.
-- PK
Rhenium
Member posted 04-27-99 11:52 AM
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Psychokitty : I have the paper, here is a very brief summary of the main part of the (slightly) relevant experimental.
A mixture of 0.79g of copper powder, 9 g of allyl chloride and 175 g of guaiacol acetate was heated in a glycerol bath for 14 hrs at 150-160 degrees C. After this time, a further 20 g of allyl chloride was added at such a rate that the temperature remained in the range given. After the completion of the heating process, the mixture was passed through a column containing 50 g of anion-exchanger (to remove HCl [my note]), and this was washed with 50 mL of ether three times. The filtrate was dried with MgSO4 and fractionated. (My notes : The authors analysed their different fractions by GC and never isolated their compounds individually. There was apparently much [~131 g] unchanged starting material (guaiacol acetate).
In this paper the authors do not actually perform the allyation of catechol. The reference they give appears to be
W.H. Perkin and V.M. Trikojus, J. Chem Soc., 1927, pg 1663.
I think that you would be better off looking at Org. Synth., III, pg 418 for a related synthesis (in good yield) of o-eugenol, or the above reference which I have not yet investigated.
Rhenium
psychokitty
Member posted 05-10-99 11:12 PM
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This proceedure details the claisen rearrangement. If it truly works, catechol could become a direct precursor to allypyrocatechol, and the method employed to synthesize it would be simple.
--PK
Rhodium
Administrator posted 05-10-99 11:22 PM
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The synth is also in The Complete Book of Ecstasy. Unfortunately, the main product is 3-allylcatechol (say 2/3 or so).
bloodgod100
Member posted 05-27-99 01:44 AM
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What about one of the techniques that oxidizes phenol to catechol used on chavicol to produce allylpyrocatechol? Isn't chavicol (found in West Indian Bay oil) phenol but with that ever-so-desirable allyl side chain?
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