Diethyl Ether → 2-Ethyl-4-(hydroxymethyl)phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-ethyl-4-hydroxybenzaldehyde (4.7 g, 26 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added dropwise 1 M LiAlH4 in Et2O (52 mL, 52.2 mmol). The resulting mixture was stirred at 0° C. for 2 h and then quenched by cautious addition of water and stirred for 15 minutes. The reaction mixture was then absorbed onto silica and loaded onto a silica pad which was washed with EtOAc. The EtOAc washings were collected and concentrated in vacuo to afford the title compound as a colourless oil (3.67 g).

Provenance & Evidence