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Synthesis of [3–12′,4′,5′-triethoxybenzoyl-(carbonyl-14C)] propionic acid (AA-149-14C)

✍ Scribed by Nobuyoshi Hayashi; Tadashi Toga; Tadakazu Murata

Publisher
John Wiley and Sons
Year
1974
Tongue
French
Weight
196 KB
Volume
10
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of 3‐[ 2′,4′,5′‐triethoxybenzoyl‐(carbonyl‐^14^C)]‐propionic acid (VII) is described. Chloroacetonitrile‐^14^C (IV) was prepared from chloroacetic‐1‐^14^C acid (I) according to the well‐known procedure. IV was reacted with 1,2,4‐triethoxybenzene in the presence of ZnCl~2~ and HCl, and the resulting ketoimine hydrochloride was hydrolyzed to 2′,4′,5′‐triethoxyphenacyl‐(carbonyl‐^14^C) chloride (V) in 66.5% yield. VII was obtained in 66% from ethyl [2′,4′,5′‐triethoxyphenacyl‐(carbonyl‐^14^C)] malonate (VI) which had been prepared in 57% from V by an application of malonic ester synthesis. The overall radiochemical yield from I to VII was 11.2%.

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