2-methyl-4-sulfanylphenol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 0.8 g, 21 mmol) and tetrahydrofuran (30 ml) was added dropwise a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (1.1 g, 6.6 mmol) in tetrahydrofuran (THF 30 ml) at 0° C. (cooled with chilled water). After 30 min of stirring at 0° C. and another 2 hours of stirring at room temperature, the reaction was quenched by addition of broken ice in an ice water bath. The value of pH of the mixture was adjusted to 3-4 by adding 6 N hydrochloric acid, and then the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml), dried over anhydrous magnesium sulfate, filtrated, and evaporated in vacuo to yield a crude product of 3-methyl-4-hydroxy-mercaptobenzene (yellow liquid). of stirring at room temperature the reaction was quenched by addition of broken ice in an ice water bath by adding 6 N hydrochloric acid the aqueous phase was extracted with ethyl acetate (3×100 ml) The combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml) dried over anhydrous magnesium sulfate filtrated evaporated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml three-necked flask with a constant-pressure dropping funnel, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.3 mmol) and tetrahydrofuran (30 ml) was added dropwise at 0° C. a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (1.7 g, 10.3 mmol) in tetrahydrofuran (THF, 30 ml). After 30 min of stirring at 0° C. and another 2 hours of stirring at room temperature, the reaction was quenched by addition of broken ice in an ice water bath. The value of pH of the mixture was adjusted to 3-4 by adding 6 M hydrochloric acid, and then the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml), dried over anhydrous magnesium sulfate, filtrated, and evaporated in vacuo to yield a crude product of 3-methyl-4-hydroxy-mercaptobenzene (yellow liquid). In a 250 ml three-necked flask with a constant-pressure dropping of stirring at room temperature the reaction was quenched by addition of broken ice in an ice water bath by adding 6 M hydrochloric acid the aqueous phase was extracted with ethyl acetate (3×100 ml) The combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml) dried over anhydrous magnesium sulfate filtrated evaporated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the mixture was warmed up to room temperature stirred for 1 hour at room temperature The reaction was quenched by adding ethanol (10 ml) 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 evaporated in vacuo