Citric Acid → 1-Naphthaldehyde

Participants

Reaction Steps

To a cold (−78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2Cl2 (200 mL) was added dropwise dry DMSO (11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (10.0 g, 0.063 mol) in dry CH2Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min, and then Et3N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10% aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added, and the mixture was filtered. Concentration provided a pale orange oil (9.7 g).

Provenance & Evidence