Benzyl Alcohol → 1-(Phenylmethyl) butanedioate

Participants

Reaction Steps

A solution of benzyl alcohol (0.52 mL, 5 mmol) in THF (20 mL) was treated with NaH (60%, 0.2 g, 5 mmol) and succinic anhydride (0.502 g, 5 mmol) and refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with H2O and extracted with EtOAc several times. The combined organic layer was washed H2O and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (1:1) as eluant to give 20 as white solid (0.866 g, 57%).

Provenance & Evidence