Acetic Acid → 1-Cyclohexyl-3-(2-hydroxy-3-methylphenyl)-1,3-propanedione

Participants

Reaction Steps

2-Acetyl-6-methylphenyl cyclohexanecarboxylate (5.2 g) was dissolved in anhydrous tetrahydrofuran (50 ml) and to the solution was added 60% sodium hydride (880 mg) by portions with stirring at room temperature. After stirring under reflux for 2 hours, the mixture was poured into cold water, acidified with acetic acid and then extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and then concentrated under reduced pressure to obtain the title compound (5.2 g) as crystals in a quantitative yield. The crystals were recrystallized from methanol to obtain the prisms, m.p. 42°-43° C.

Provenance & Evidence