p-Toluenesulfonic acid → HCID 14664466, compound

Participants

Reaction Steps

Methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (3.5 g, 15.5 mmol), copper sulphate anhydrous (4.3 g, 27 mmol, 1.8 equiv.) and acetone (40 ml, excess) were stirred in the presence of a catalytic amount of para-toluene sulphonic acid at 35° C. After 16 hours, the copper sulphate was removed by filtration, and the filtrate was removed and evaporated to dryness on a rotary evaporator. The product was purified by flash column chromatography using DCM as eluant. Evaporation of the appropriate fractions left methyl 5-(4-methoxyphenyl)-2,2-dimethyl -1,3-dioxolane 4-carboxylate as a clear, colourless oil (4.0 g, 96%). [a]D=+37.4° (THF, conc.=0.01712, 20° C). 1H-NMR was in accordance with expected signals.

Provenance & Evidence