Diethyl Ether → 4-(1-Methylpropoxy)phenoxyacetonitrile

Participants

Reaction Steps

To prewashed sodium hydride (1.01 g, 42.0 mmol) in 60 ml of DMF at 20° is added 4-(1-methylpropoxy)phenol (7.0 g, 42.0 mmol) in 5 ml of DMF over 30 min. After 1 hour at RT, chloroacetonitrile (3.80 g, 50.4 mmol) in 5 ml of DMF is added dropwise to the mixture at 5°-8° over 15 min. After addition, the reaction is warmed slowly to RT and stirred at RT for 18 hours. The mixture is then poured into ice water and ether and extracted with ether (3X). The combined organic phases are washed with 10% NaOH, with water until neutral and with brine, dried, filtered and solvent removed in vacuo to give 4-(1-methylpropoxy)phenoxyacetonitrile.

Provenance & Evidence