Potassium Carbonate → HCID 53638351, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2-chloro-6-hydroxybenzaldehyde (4.4 g), (R)-glycidyl 4-toluenesulphonate (5.0 g) and potassium carbonate (3.9 g) in dimethylformamide (120 ml) was heated at 60° C. for 5 hours then allowed to stand at ambient temperature for 18 hours. The solvent was removed in vacuo, water (60 ml) was added and the mixture extracted with ether (3×100 ml). The combined extracts were dried over magnesium sulphate and the solvent evaporated. The residue was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane followed by a 19:1 mixture of dichloromethane and industrial methylated spirit. Appropriate fractions were combined and the solvent was removed in vacuo to give (R)-2-chloro-6-(2,3-epoxypropoxy)benzaldehyde (2.8 g) m.p. 62-64° C.

Provenance & Evidence