Oxalyl chloride → HCID 22326173, compound

Participants

Reaction Steps

25.2 g (93 mmol) monophenylethyl (−)-phthalate was heated at reflux in 50 ml oxalyl chloride (3 eq.) for 2 h. The excess oxalyl chloride was distilled under vacuum. The crude acid chloride was then diluted in 100 ml THF cooled to 0° under argon, and 7.4 g (2 eq.) NaBH4 was added. The reaction mixture was maintained under stirring at ambient temperature for 1 h, then cooled to 0° and 20 ml of methanol was added. After leaving the reaction mixture under stirring at ambient temperature for 1 h it was poured over cold 5% KHSO4 then extracted using diethyl ether. Chromatography of the crude product over silica gel (9:1 toluene/ether) yielded 12.1 g (47%) 2-phenylethyl 2-hydroxymethylbenzoate containing about 9% phthalide in the form of a white solid.

Provenance & Evidence