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Synthesis of [3–12′,4′,5′‐triethoxybenzoyl‐(carbonyl‐ 14 C)] propionic acid (AA‐149‐ 14 C)
Author(s) -
Hayashi Nobuyoshi,
Toga Tadashi,
Murata Tadakazu
Publication year - 1974
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590100410
Subject(s) - chloroacetic acid , chemistry , yield (engineering) , malonic acid , malonate , hydrolysis , hydrochloride , medicinal chemistry , chloride , diethyl malonate , alkaline hydrolysis , organic chemistry , nuclear chemistry , catalysis , materials science , metallurgy
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%.