Water → 4-(2-Hydroxy-2-methyl-propoxy)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL), 4-hydroxybenzonitrile (2.0 g, 16.8 mmol), potassium carbonate (9.3 g, 67.3 mmol), water (6 mL) and ethanol (60 mL) was heated at 80° C. overnight. The reaction mixture was cooled, concentrated in vacuo and residue was diluted with ether (200 mL) and filtered. The filtrate was washed with water (50 mL) and brine solution (50 mL). The organics were separated and dried over MgSO4 and purified by silica gel column chromatography using 0-100% EtOAc/DCM as eluent to give 4-(2-hydroxy-2-methyl-propoxy)benzonitrile (3.0 g, 94%) as a yellow solid. ESI-MS m/z calc. 191.1. Found 192.3 (M+1)+; Retention time: 1.05 minutes (3 min run).

Provenance & Evidence