Dichloromethane → 2-Phenylindan

Participants

Reaction Steps

To a stirred two phase solution of dichloromethane (1 L) and 15% NaOH (750 mL) were added alpha, alpha,-di-bromo-o-xylene (100 g, 0.38 mol), benzyl cyanide (44.3 g, 0.38 mol) and benzyltriethylammonium chloride (17.2 g, 0.075 mol). The two phase solution was vigorously stirred at ambient temperature for 48 hours, at which time benzyl cyanide (20 g, 0.17 mol), benzyltriethylammonium chloride (9.0 g, 0.039 mol), and 15% NaOH (300 mL) were added. The mixture was stirred for an additional 48 hours. The reaction was poured into water (1 L) and extracted with ether (2.5 L). The organic solution was washed with water (3×1 L), brine (500 mL), dried over magnesium sulfate and the solvents evaporated. Vacuum distillation of the residue gave 42.6 g of 2,3-dihydro-2-phenyl-1H-indene- 2-carbontrile, bp 166°-168° C. (5 mm), Lit. bp 160°-180° C. ( 1 mm), as a colorless oil.

Provenance & Evidence