Reacción #157262

Ecuación de reacción

lithium aluminum tetrahydride

2,5-dimethyl-4-hydroxy-phenyl thiocyanic acid

→

2,5-dimethyl-4-hydroxy-mercaptobenzene

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm up to room temperature
2. 2
   workup.STIRRINGstirred for another 1 hour at room temperature
3. 3
   OtroThe reaction was quenched
4. 4
   workup.ADDITIONby adding ethanol (10 ml)
5. 5
   workup.ADDITIONby adding 6 M hydrochloric acid in an ice water bath
6. 6
   Extracciónthe aqueous phase was extracted with ethyl acetate (3×60 ml)
7. 7
   SecadoThe combined organic layer was dried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltrated
9. 9
   Otroevaporated in vacuo

Procedimiento

In a 250 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.3 mmol) and tetrahydrofuran (40 ml) was added dropwise a solution of 2,5-dimethyl-4-hydroxy-phenyl thiocyanic acid (1.2 g, 6.7 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 3-4 by adding 6 M 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 2,5-dimethyl-4-hydroxy-mercaptobenzene (yellow liquid).

Fuente