Methyl Acrylate → dimethyl 4-cyano-4-phenylheptanedioate

Participants

Reaction Steps

Phenylacetonitrile (11.7 g, 0.1 mole) and methyl acrylate (47 ml, 0.5 mole) were added to tert-butanol (60 ml) and heated to boiling point. The source of heat was then removed. Triton B (benzyltrimethylammonium hydroxide, 40% in methanol, 15.2 ml) dissolved in tert-butanol (23 ml) was added dropwise, first of all slowly and then at a faster rate. After the dropwise addition the reaction mixture was boiled under reflux for 4 hours. The reaction mixture was cooled to room temperature overnight. The reaction mixture was worked up by adding toluene (100 ml) and water (70 ml). The organic phase was separated and washed with water (1×70 ml) and saturated sodium chloride solution (1×50 ml). After drying over Na2SO4, the solvent was distilled off in a fume cupboard on account of the strong smell. Purification was carried out by bulb tube distillation at a pressure of 7.8×10−2 mbar and at a temperature of 235° C. The desired 4-cyano-4-phenylheptanedioic acid dimethyl ester was obtained in a yield of 21.45 g (72%) as a colourless viscous substance.

Provenance & Evidence