Water → 5-Hydroxy-2-(3-methoxymethoxypropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Participants

Reaction Steps

5.0 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71) were dissolved in 40 ml of dimethylformamide, and 260 mg of a 55% w/w oily suspension of sodium hydride was added at room temperature. The reaction mixture was then heated for 1 hour at 40°-45° C., after which it was cooled with ice-water, and then a solution of 1.6 g of chloromethyl methyl ether in 5 ml of benzene was added dropwise. After completion of the addition, the temperature of the mixture was gradually raised and then the mixture was heated for 1 hour at 50°-55° C. The reaction mixture was then poured into water and extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel Lobar column chromatography, and the title compound was obtained from the fraction eluted with a 100:3 by volume mixture of benzene and ethyl acetate.

Provenance & Evidence