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

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Reaction Steps

Two ml 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 followed by solvent evaporation. The residue was partitioned between 400 ml of ether and 100 ml 1 N NaOH. The remaining ether layer was washed with 100 ml H2O and with 100 ml brine, dried (MgSO4) and evaporated to yield 31.2 gm of crude 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile.

Provenance & Evidence