Potassium Hydroxide → 2-(4-Fluorophenyl)propanenitrile

Participants

Reaction Steps

A mixture of 68 parts of 4-fluorobenzeneacetonitrile, 180 parts of ethyl carbonate, 100 parts of a sodium methoxide solution 30% and 200 parts of dimethylbenzene was distilled till an internal temperature of 110° C. was reached. The distillate was cooled and 80 parts of 2-propanol were added, followed by the dropwise addition of 63 parts of methyl sulfate at room temperature (exothermic reaction: temperature rose to 80° C.). The remaining 120 parts of 2-propanol were added while stirring vigorously. Upon completion, stirring was continued for 20 hours. Then there were added 56 parts of potassium hydroxide (exothermic reaction: temperature rose to 75° C.). The whole was stirred and refluxed for 30 minutes. The reaction mixture was cooled and poured into 750 parts of water. The aqueous phase was separated and extracted with methylbenzene. The extract was dried, filtered and evaporated. The oily residue was distilled, yielding 54 parts of 4-fluoro-α-methylbenzeneacetonitrile; bp. 110°-115° C. at 11 mm. pressure (intermediate 1).

Provenance & Evidence