Diethyl Ether → Benzyl methyl carbonate

Participants

Reaction Steps

Benzyl chloride (31.65 g, 0.25 mole), dimethyl carbonate (90.0 g, 1.0 mole), tetra-n-butylphosphonium bromide (3.39 g, 0.01 mole) and N,N-dimethylformamide (200 ml) are heated to 117° C.-118° C. for 6 hours. After heating is discontinued the reaction mixture is added to 300 ml of diethyl ether and 300 ml of water. The organic layer is washed with 3×100-ml allotments of water followed by 2×100 ml-portions of 10 percent aqueous HCl, 100 ml of saturated aqueous NaHCO3 and 100 ml of a saturated aqueous NaCl solution, and dried over MgSO4. After solvent removal, distillation gives 27.02 g (65 percent yield based on benzyl chloride) of benzyl methyl carbonate, b.p. 110° C.-111° C. (11 torr).

Provenance & Evidence