Water → (4-Fluoro-3-phenoxyphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry of 1.4 grams (0.0375 mole) of 95% lithium aluminum hydride in 50 mL of diethyl ether was added dropwise during a one hour period a solution of 21.6 grams (0.1 mole) of 4-fluoro-3-phenoxybenzaldehyde in 50 mL of diethyl ether. Upon completion of addition the reaction mixture was heated at reflux for one hour. The reaction mixture was then cooled to 15° C., and 1.4 mL of water was cautiously added dropwise. Upon completion of addition the reaction mixture was again cooled to 15° C., and sequentially 1.4 mL of aqueous 15% sodium hydroxide and 4.2 mL of water were added. The reaction mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure yielding 19.5 grams of 4-fluoro-3-phenoxyphenylmethanol.

Provenance & Evidence