2-Hydroxy-5-methylacetophenone → HCID 18950993, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-hydroxy-5-methylphenyl)ethanone (1 g) in DMF (7 ml) was added to a solution of sodium methoxide (0.39 g) in ethanol (7 ml). After about 10 min a solution of 2-(bromomethyl)benzonitrile (1.3 g) in DMF (7 ml) was added and the solution heated to 110° C. After 2 h further sodium methoxide (0.39 g) was added and heating at 110° C. continued. After a further 30 min, the reaction was cooled to room temperature and the ethanol evaporated. The solution was poured into water/ice (200 ml) and extracted into ethyl acetate (4×30 ml). The combined organic extracts were washed with water (4×20 ml) and dried. Filtration and evaporation gave a yellow oil which was then dissolved in dichloromethane (2 ml) and methanol (30 ml). Concentration gave a solid which was collected and washed with further methanol to give the title compound as a white solid (0.53 g).

Provenance & Evidence