Dichloroacetic Acid → HCID 69820753, compound

Participants

Reaction Conditions

Reaction Steps

A mixture that consists of 54.1 g (100 mmol) of 2,3,4,6-tetra-O-benzyl-benzylgalactopyranose, 1.64 g (15 mmol) of tetramethylammonium chloride in 350 ml of toluene and 200 ml of 60% aqueous sodium hydroxide solution is cooled to 0° C. At 0° C., 52.7 g (130 mmol) of 2-(4,4′-dimethoxytriphenylmethyloxy)-ethylbromide, dissolved in 100 ml of toluene, is added in drops over 30 minutes while being stirred vigorously. It is stirred for three hours at 0° C. 300 ml of toluene is added, the organic phase is separated, and the aqueous phase is extracted twice with 200 ml of toluene. The solvent is distilled off in a vacuum. The residue is taken up in 500 ml of dichloromethane, and 25 g (194 mmol) of dichloroacetic acid is added. It is stirred for three hours at 35° C. The solution is washed three times with 300 ml of 10% aqueous sodium hydroxide solution, and the organic phase is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1).

Provenance & Evidence