Benzene → HCID 13037779, compound

Participants

Reaction Steps

To 22 ml of dry benzene there was added, under nitrogen atmosphere, 1.68 g (31.2 mMol) of sodium methoxide. There was then slowly added with stirring a solution of 6.06 g (30 mMol) of the 4-cyclohexyl acetophenone prepared in Step A above and 3.54 g (30 mMol) of freshly recrystallized dimethyl oxalate in 40 ml of benzene. The reaction mixture was cooled and soon after addition a yellow crystalline precipitate formed. The reaction mixture was allowed to warm to room temperature and stirred for an additional hour. There was then added 75 ml of ether and 24 ml of 2 N hydrochloric acid with 6 ml of water. The mixture was shaken for about 15 minutes, until all of the solid dissolved. The organic layer was then separated, washed with a small amount of water, and dried over magnesium sulfate. The solvent was then evaporated, the residue partially crystallized on cooling, and then crystallized from 3:1 petroleum ether:benzene. After cooling, 3.33 g of yellow solid product, m.p. 96°-98° C., was filtered off.

Provenance & Evidence