Menthol → Butanoic acid, 3-oxo-, 5-methyl-2-(1-methylethyl)cyclohexyl ester

Participants

Reaction Steps

A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of menthol and 100 mg of sulfated tin oxide catalyst prepared according to example 1 above, in 20 ml of toluene was heated to 110° C. in a two necked round bottom flask provided with a distillation condenser to remove methanol. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction (about 6 hours), the catalyst was filtered and the filtrate was concentrated and chromatographed on a silica gel column (95% petroleum ether and 5% ethyl acetate) to afford menthyl acetoacetate as a viscous colorless liquid in 91% yield.

Provenance & Evidence