Reaktion #157260

Reaktionsgleichung

lithium aluminum tetrahydride

3-methyl-4-hydroxy-phenyl thiocyanic acid

→

3-methyl-4-hydroxy-mercaptobenzene

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 250 ml three-necked flask with a constant-pressure dropping
2. 2
   workup.STIRRINGof stirring at room temperature
3. 3
   Sonstigethe reaction was quenched by addition of broken ice in an ice water bath
4. 4
   workup.ADDITIONby adding 6 M hydrochloric acid
5. 5
   Extraktionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
6. 6
   WaschenThe combined organic layer was washed with a saturated solution of sodium chloride (2×100 ml)
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltrated
9. 9
   Sonstigeevaporated in vacuo

Vorschrift

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).

Quelle