Water → 4-Mercapto-2-methylphenol

Temperatur

0 °C

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).

1. stirringof stirring at room temperature
2. customthe reaction was quenched by addition of broken ice in an ice water bath
3. additionby adding 6 N hydrochloric acid
4. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
5. washThe combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltrated
8. customevaporated in vacuo

ORD-Eintrag

ord-032bc698151a4a73af28dc680686db87

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822519B2