Methanol → HCID 2750802, compound

Participants

Reaction Steps

o-Nitromandelic acid (5 g.) and thionyl chloride (50 ml.) were mixed, heated under reflux on a steam bath for 1 hour and cooled, then the excess of thionyl chloride was removed on a rotary evaporator at room temperature. The crude o-nitromandeloyl chloride thus obtained was carefully mixed with methanol (70 ml.), and after the initial vigorous reaction had subsided, the mixture was heated under reflux on a steam bath for 1 hour, cooled, and the solvent evaporated under reduced pressure. The oil thus obtained was chromatographed on silica, and elution with diethyl ether/petroleum ether (b.p. 60°-80° C.), 6:4 by volume yielded methyl o-nitromandelate. The methyl o-nitromandelate thus obtained was reduced by the general process described under (a) above to give the required starting material;

Provenance & Evidence