O-Cresol → Benzene, 1-methyl-2-(1-methylethoxy)-

Participants

Reaction Steps

To a solution of 54.1 g (0.5 mole) of ortho-cresol in 150 ml of DMSO was added portionwise and with stirring 12 g of 57% sodium hydroxide. This addition was exothermic to 45° C. After 2 hours at ambient temperature, 61.5 g (0.5 mole) of isopropyl bromide in 50 ml of DMSO was added dropwise with stirring. After another 2 hours, the reaction mixture was poured into 1000 ml of ice water and extracted with ether. Distillation of the dried extract gave 53.9 g of product as a colorless liquid; b.p. 94°-96° C. (30 mm).

Provenance & Evidence