Water → 3-(2,2-Dimethoxyethylthio)phenol

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Reaction Steps

The S-sodium salt of 3-mercaptophenol prepared in Example 7 was dissolved in dimethylformamide (25 ml) and charged under nitrogen gas into a glass reaction vessel equipped with a mechanical stirrer, thermometer and addition funnel. The solution was heated to a temperature of 45 to 50° C., and 1-chloro-2,2-dimethoxyethane (3.15 grams) was added with stirring. After the addition was completed, stirring was continued for a period of about 3 hours. After this time the reaction mixture was poured into water (150 ml), and the resulting mixture was carefully neutralized with ammonium chloride. The mixture was then extracted with chloroform and the organic phase was separated. The organic portion was washed with water and then dried with phase separation paper. The dried solution was then stripped of solvent, leaving an oil. This oil was distilled, and the fraction boiling at 138° to 144° C. at 0.04 mm of Hg pressure was collected to yield the desired product 3-(2,2-dimethoxyethylthio)phenol.

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