Oxalyl chloride → HCID 7021752, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (3.6 ml) was added to a solution of 2-benzyloxy-4-methylbenzoic acid (9.02 g) in dichloromethane (20 ml), one drop of DMF was added and the mixture was stirred for 2 hours then evaporated to dryness. The residue was dissolved in diglyme (70 ml) and cooled to -78° C. under argon. Lithium-tri-t-butoxyaluminohydride (78 ml of 0.5M solution in diglyme) was added at such a rate that the temperature did not exceed -60° C. The mixture was stirred below this temperature for 2 hours and was then poured carefully onto ice and acidified with concentrated HCl. The mixture was extracted with diethylether (3×150 ml) and the gum obtained on work up was subjected to chromatography on silica eluted with dichloromethane to give 2-benzyloxy-4-methylbenzaldehyde (3.73 g).

Provenance & Evidence