Ethylene Glycol → HCID 178421610, compound

Participants

Reaction Steps

A solution of 4-acetylphenylthioacetic acid (8.4 g, 40 mmol) (obtained as described by Walker and Leib in J. Org. Chem. 1963, 28, 3077-3082), ethylene glycol (4.96 g, 80 mmol) and a catalytic quantity of p-toluenesulphonic acid in benzene (80 ml) was heated at reflux for 16 hours using a Dean and Stark apparatus. Water (1.5 ml, 80 mmol) was collected. The solvent was removed by evaporation to give an oil. Ethanol (30 ml) and 2N sodium hydroxide solution (1 equivalent) were added and the mixture was stirred for one hour. The mixture was concentrated in vacuo. The residue was diluted with water to give a volume of 80 ml. Ether (50 ml) was added and the mixture was stirred vigorously with cooling in ice. A 10% aqueous solution of citric acid was added to give a pH of 6.5. The mixture was extracted with ether (20×50 ml). The combined extracts were dried (N2SO4) and the solvent was removed by evaporation to give a white solid. Water was added to the solid and the mixture was stirred. The solid was collected by filtration and dried in vacuo over phosphorus pentoxide. There was thus obtained 4-(2-methyl-1,3-dioxolan-2-yl)phenylthioacetic acid (B) as a solid (5.2 g, 51% yield); NMR spectrum (200 MHz, d6 -DMSO): 1.49(s, 3H), 3.62(m, 2H), 3.72(s, 2H), 3.9(m, 2H), 7.25(m,4H).

Provenance & Evidence