p-Toluenesulfonic acid → 3-(3-Methylcyclohex-1-en-1-yl)thiophene

Participants

Reaction Steps

A stirred solution of 37.6 g (0.192 mol) of 1-(3-thienyl)-3-methylcyclohexanol and 0.5 g of p-toluenesulfonic acid in 200 mL of toluene was heated under reflux, and by-product water was collected in a Dean-Stark trap attached to the reaction vessel. After about 16.5 hours, the reaction mixture was cooled and concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 11.6 g of 3-methyl-1-(3-thienyl)cyclohexene b.p. 105° C.±5° C./0.25 mm.

Provenance & Evidence