Ethanethiol (1.25g, 1.5 ml, 0.02 mole) dissolved in N, N- dimethyl-formamide (20 ml) is added to a suspension of sodium hydride (1 g of 50%oil dispersion) in dry DMF (10 ml) under an atmosphere of nitrogen. The mixture is stirred for 5 min under anhydrous conditions. A solution of phloroglucinol trimethyl ether (1.14) (1 g,0.006 moles) in dry DMF (10 ml)is added, and the mixture is refluxed for 3 hr. The reaction mixture is cooled and acidified with hydrochloric acid (10%). It is extracted with ether(3 x 50 ml). The ether extract is washed with water and extracted with sodium hydroxide solution (5%). The clear alkaline extract is acidified with hydrochloric acid. The mixture is extracted with ether. The ether extract is washed with water, ried (anhydrous sodium sulphate), and drilled. 3,5-Dimethoxyphenol is obtained as an oil. Yield 0.9 g (98.1%).B.p.198-199°/30 mm.
