Kikumasa Sato, Seiichi Inoue, Masao Ohashi
1974
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A New synthesis of 2-hydroxy-3-methyl-2-cyclohexen-1-one (Ia), a flavor component of coffee aroma, is described. The selenium dioxide oxidation of ethyl 1-methyl-2-oxocyclohexanecarboxylate (IIa) gave α-diketone (IIIa), which was then hydrolyzed and decarboxylated to afford Ia. The treatment of IIa with cupric chloride in 50% acetic acid also yielded Ia. The dimethyl sulfoxide oxidation of ethyl 3-bromo-1-methyl-2-oxocyclohexanecarboxylate (IV) afforded IIIa, along with 3-bromo-6-ethoxycarbonyl-2-hydroxy-6-methyl-2-cyclohexen-1-one (V). The halogenation of IIa produced dihalogeno ketoesters (VIa) (VIIa), which also yielded Ia in a pure state by means of a direct acidic hydrolysis or by a two-step hydrolysis using morpholine. Other allied compounds are also described.