Aluminium lithium hydride → 3-Ethyl-4-hydroxy-mercaptobenzene

Temperature

0 °C

In a 150 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.2 mmol) and tetrahydrofuran (40 ml) was added dropwise a solution of 3-ethyl-4-hydroxy-phenyl thiocyanic acid (1.3 g, 7.25 mmol) in 20 ml tetrahydrofuran at 0° C. After 30 min of stirring at 0° C., the mixture was allowed to warm up to room temperature and then stirred for another 1 hour at room temperature. The reaction was quenched by adding ethanol (10 ml). The value of pH of the mixture was adjusted to pH 3-4 by adding 6 N hydrochloric acid in an ice water bath, and then the aqueous phase was extracted with ethyl acetate (3×60 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and evaporated in vacuo to yield the crude product of 3-ethyl-4-hydroxy-mercaptobenzene (yellow liquid).

1. temperatureto warm up to room temperature
2. stirringstirred for another 1 hour at room temperature
3. customThe reaction was quenched
4. additionby adding ethanol (10 ml)
5. additionby adding 6 N hydrochloric acid in an ice water bath
6. extractionthe aqueous phase was extracted with ethyl acetate (3×60 ml)
7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltrated
9. customevaporated in vacuo

ORD record

ord-b4c25ad37af143c9878ff4be02a5494a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822519B2