Dimethyl Sulfoxide → Benzenepentanal

Participants

Reaction Steps

Under nitrogen atmosphere, at −78° C., to a stirred solution of oxalyl chloride (0.53 mL, 6.17 mmol) in dry CH2Cl2 (12 mL), DMSO (0.40 mL, 5.7 mmol) was added in a fast manner. After 15 min, a solution of 5-phenylpentan-1-ol (0.78 g, 4.75 mmol) in dry CH2Cl2 (6 mL) was added. The reaction mixture was stirred for 2 h at −78° C. before addition of Et3N (1.98 mL, 14.24 mmol). The solution was allowed to warm at rt, and after evaporation of CH2Cl2 the residue was taken up in Et2O and a saturated NH4Cl solution. After separation of phases the organic fraction was dried over Na2SO4, filtered and concentrated to dryness affording the title compound (0.75 g, 97%) as a pure product. 1H NMR (CDCl3): δ 1.67-1.73 (m, 4H), 2.44-2.52 (m, 2H), 2.60-2.71 (m, 2H), 7.16-7.35 (m, 5H), 9.78 (t, J=1.8 Hz, 1H).

Provenance & Evidence