((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrile → 4-Mercapto-2-methylphenol

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In a 500 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 3.5 g, 92.2 mmol) and tetrahydrofuran (THF, 50 ml) was added dropwise a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (6.13 g, 37.1 mmol) in tetrahydrofuran (THF, 30 ml) at 0° C. After 30 min of stirring at 0° C., the mixture was warmed up to room temperature and then stirred for 1 hour at room temperature. The reaction was quenched by adding ethanol (10 ml), The value of pH of the mixture was adjusted to 3-4 by adding 6 M hydrochloric acid in an ice water bath. Then the aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and evaporated in vacuo to give a crude product 4-hydroxy-3-methyl thiophenol as yellow oil.

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