Sciencemadness Discussion Board

Aldol condensation of protocatechualdehyde with acetone and MEK.

phendrol - 6-10-2014 at 01:11

Will protocatechualdehyde condense with acetone or MEK? I couldn't find anything using the search engine or even google. Just information about other aldehydes but nothing on protocatechualdehyde.

I know that the end compund depends on the catalyst used. What would be the products from condensing it with acetone or MEK, using either basic or acidic catalyst?

I have around 50 grams of the above mentioned aldehyde and I don't want to experiment yet, because I don't really know what I can expect.

solo - 6-10-2014 at 05:56

.....here is another inquiry with some idea as to where he was going....solo

http://www.sciencemadness.org/talk/viewthread.php?tid=6506


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Reference Information

PHOTO-REIMER-TIEMANN REACTION OF
PHENOLS, ANILINES AND INDOLINE

K. HIRAO, M. IKEGAME and O. YONEMITSU
Tetrahedron
Vol. 30. pp. 2301 to 2305


Abstract
The photo-reaction of phenol (1) with chloroform in the presence of diethylamine gave salicylaldehyde (2) and 4-hydroxybenzaldehyde (3) in fair yield. Dihydroxybenzenes, sensitive to alkali, under similar conditions without the base gave corresponding aldehydes and a cyclohexa-2.5dienone
(15). The photo-reaction was also applied to diethylaniline (18), indoline (21) and N-methylindoline (24). In carbon tetrachloride instead of chloroform in an alcohol solution the same
type of reaction took place to give esters. The mechanism involving the coupling of a phenoxy radical or a radical cation with dichloromethyl radical and not involving dichlorocarbene is proposed.







Ueber Synthese der Sinapinsäure
C. Graebe and E. Martz
Berichte der deutschen chemischen Gesellschaft
Volume 36, Issue 1, pages 1031–1033, Januar–März 1903



[Edited on 6-10-2014 by solo]

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phendrol - 8-10-2014 at 01:30

Piperonal is not what I am interested in. Even thou it smells nice.