Re: ORGLIST: reduction

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From: Dr Jost T Bohlen (bohlen$##$fiz-chemie.de)
Date: Tue Oct 06 1998 - 04:21:54 EDT




Jim Sims wrote:

> I would like to prepare a sample of p-coumaraldehyde
> (4-hydroxycinnamaldehyde). p-Coumaric acid (4-hydroxycinnamic acid) is
> available. Does anyone have a suggestion for a simple, high-yielding
> method which might be used? Thanks in advance.
>
> Professor Jim Sims
> Department of Plant Pathology
> University of California, Riverside
> Riverside, CA 92521
> Voice: 909 787 4127
> FAX 909 787 4294
>
> __________________

> According to the ChemInform Reaction Library the route via p-Cinnamic
> acid derivatives does not look very promising. Better yields are obtained
> by oxidizing the corresponding alcohols. However, there are hardly any
> examples involving coumaric acid derivatives.

A lot more syntheses are published starting with p-hydroxy-benzaldehydes.
Try for example
Daubresse, N.; Francesch, C.; Mhamdi, F.; Rolando, C.; Synthesis 1994 (4),
369-371 or
Cabezas, J. A.; Oehlschlager, A. C.; Tetrahedron Lett 1995, 36 (29),
5127-5130.

Good luck,
Jost


Dr Jost T Bohlen
Product Manager ChemInform
FIZ CHEMIE BERLIN




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