J. A. McRae, E. Charlesworth, F. R. Archibald
Sep 1, 1943
Citations
0
Influential Citations
2
Citations
Journal
Canadian journal of research
Abstract
2-Oxotetrahydrofuran-3-acetic acid is produced when ethylene oxide, ethyl sodiomalonate, and ethyl chloroacetate are condensed and the resulting ester is hydrolysed and decarboxylated. If ethyl β-bromopropionate is used in place of ethyl chloroacetate, 2-oxotetrahydrofuran-3-propionic acid results.Condensation of propylene oxide with ethyl malonate in the presence of sodium ethylate, followed by hydrolysis and decarboxylation, yields γ-valerolactone (2-oxo-5-methyltetrahydrofuran) in rather poor yield.The β-halogenated esters may be replaced in condensations of this nature by benzyl chloride, 2-oxo-3-benzyltetrahydrofuran being produced.