Aluminium lithium hydride → 2,5-Dimethyl-4-sulfanylphenol
Reaction equation
[H-].[H-].[H-].[H-].[Al+3].[Li+].[CH3:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([CH3:15])=[CH:10][C:9]=1[S:16]C#N>O1CCCC1>[CH3:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([CH3:15])=[CH:10][C:9]=1[SH:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- temperatureto warm up to room temperature
- stirringstirred for another 1 hour at room temperature
- customThe reaction was quenched
- additionby adding ethanol (10 ml)
- additionby adding 6 M hydrochloric acid in an ice water bath
- extractionthe aqueous phase was extracted with ethyl acetate (3×60 ml)
- dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltrated
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-771ad15c640f4a6db34888342be1153c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822519B2
Reaction notes
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