Trifluoroacetic acid → 4-(1-Ethoxyethoxy)-3-methoxybenzonitrile

Participants

Reaction Steps

2 ml of trifluoroacetic acid was added slowly to a chilled solution of 20 g of 3-methoxy-4-hydroxybenzonitrile, 50.7 ml of ethyl vinyl ether and 50 ml tetrahydrofuran (THF). The mixture was stirred at room temperature overnight. 7.5 ml of triethylamine was added to the mixture and stirring was continued for several minutes until the solvent was evaporated. The residue was partitioned between 400 ml of diethyl ether and 100 ml 1N NaOH. The diethyl ether layer was washed successively with 100 ml H2O and 100 ml brine, dried over MgSO4 and evaporated to yield 31.2 gm of 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile.

Provenance & Evidence