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Synthesis of [14C1]squaric acid

✍ Scribed by J. R. Heys; E. H. Chew

Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
180 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The title work proceeds in five steps and 16% overall yield from sodium [1‐^14^C]acetate, which was converted by bromination followed by ethoxide displacement and reaction with phthaloyl dichloride to ethoxy[1‐^14^C]acetyl chloride. The thermal[2+2]cycloaddition of tetraethoxyethene with ethoxy[1‐^14^C]ketene, derived from base induced elimination from ethoxy[1‐^14^]acetyl chloride following the method of Bellus, provided an 80% yield of 1‐(ethoxy[1‐^14^C]acetoxy)‐2,3,3,4,4‐pentaethoxy‐l‐[1‐^14^C]‐cyclobutene. Acid hydrolysis and liquid‐liquid extraction afforded [^14^C]squaric acid.

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