Water → 6-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

30 ml of 2-bromotoluene and 14 g (0.11 mol) of AlCl3 were introduced into a three-necked flask, cooling was carried out to 0° C. and a solution of 50 g (0.27 mol) of 2,5-dichloro-2,5-dimethylhexane in 100 ml of 2-bromotoluene was added dropwise, and the reaction mixture was permitted to heat to room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic phase was separated by settling, washed with an aqueous sodium bicarbonate solution and evaporated. The product crystallized on stirring in methanol. After filtration, 56.9 g (75%) of 2-bromo-5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene, with a melting-point of 92°-93° C., were recovered.

Provenance & Evidence