Ethyl Salicylate → HCID 19087556, compound

Participants

Reaction Steps

Ethyl salicylate (30 g, 0.18 mol) was added dropwise with stirring to a suspension of oil-free sodium hydride (5 g, 0.21 mol) in dry dimethylformamide (100 ml) under a nitrogen atmosphere. After one hour, 2,5-dichloropyridine (26 g, 0.17 mol) was added and the reaction mixture refluxed for 48 hours. The dimethylformamide was then removed in vacuo and 11 of a 50:50 (v/v) mixture of water and trichloromethane added to the remaining residue. The organic layer was separated, washed, dried and, finally, chromatographed on a silica column using trichloromethane and hexane (3:1, v/v) as eluant to give the title compound as a colourless oil (32.1 g, 0.115 mol, 64% yield).

Provenance & Evidence