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Synthesis of 2,4-dihydroxy-6-pentyl-benzoic-6-14C acid, ethyl ester. (olivetolic-6-14C acid. ethyl ester)

✍ Scribed by J. P. Schmit; V. Van de Velde; M. Piraux

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
222 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

In a first step, Δ1‐trans‐octenoic‐3‐^14^C acid was prepared by a Grignard reaction with BaCO~3~‐^14^C and 1‐bromo‐pentane, followed by reduction of the obtained hexanoic‐1‐^14^C acid to hexanal‐1‐^14^C via the n‐hexanol‐1‐^14^C. The produced hexanal‐1‐^14^C, by condensing with malonic acid gives the request Δ1‐trans‐octenoic‐3‐^14^C acid. In a second step, olivetolic‐6‐^14^C acid, ethyl ester was prepared by condensing the Δ1‐trans‐octenoic‐3‐^14^C acid, methyl ester with ethyl acetoacetate followed by bromination and catalytic hydrogenation.

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