Reaktion #157257

Reaktionsgleichung

lithium aluminum tetrahydride

3-methyl-4-hydroxy-phenyl thiocyanic acid

→

4-hydroxy-3-methyl thiophenol

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was warmed up to room temperature
2. 2
   workup.STIRRINGstirred for 1 hour at room temperature
3. 3
   SonstigeThe 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
   ExtraktionThen the aqueous layer was extracted with ethyl acetate (3×100 ml)
7. 7
   TrocknenThe combined organic layer was dried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltrated
9. 9
   Sonstigeevaporated in vacuo

Vorschrift

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.

Quelle