Benzyl Chloride → 1,3-Bis(benzyloxy)-2-methylpropan-2-ol

Participants

Reaction Steps

1 -Benzyloxymethyl-1-methyl-ethane-1, 2-diol (5g) in dimethylformamide (25 ml) was treated with sodium hydride (0.65g), the reaction mixture was stirred at ambient temperature for 1 h. then at 90° C for 15 min. The reaction mixture was cooled and benzyl chloride (3.3g) added; it was stirred for 4 h. at ambient temperature. The solvent was evaporated and the product isolated by chromatography on silica gel using methylene chloride/ether (9/1) to give the desired product as a colourless oil. The 1,3-configuration was confirmed by n.m.r. which showed the methylene groups of the carbon backbone to be equivalent, hence, establishing the symmetry of the molecule.

Provenance & Evidence