Diethyl Ether → Oxalic acid, di(2-phenylethyl) ester

Participants

Reaction Steps

Oxalyl chloride (10.2 g, 80.4 mmol) was added dropwise during 20 min to a stirred solution of 2-phenylethanol (20.0 g, 163.7 mmol) in pyridine (165 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight. Ether was added (300 mL, 2×) and the mixture extracted with H2SO4 (10%, 300 mL, 3×), a saturated solution of NaHCO3 (300 mL, 3×) and a saturated solution of NaCl (300 mL, 2×, pH 6). The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/diethyl ether 1:1) gave 20.1 g (84%) of a solid.

Provenance & Evidence