Sodium Cyanide → 2-(1-Phenylcyclohexyl)acetonitrile
Reaction equation
[C:1]1([C:7]2([CH2:13]OS(C)(=O)=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:19]#[N:20].[Na+]>CS(C)=O.O>[C:1]1([C:7]2([CH2:13][C:19]#[N:20])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
To a stirred solution of methanesulfonic acid 1-phenyl-cyclohexylmethyl ester (252) (20.0 g, 74.52 mmol) in dimethyl sulfoxide (100.0 mL) were added KI (1.24 g, 7.45 mmol) and NaCN (5.48 g, 111.78 mmol) and the reaction mixture was stirred at 140° C. for 16 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate and the organic layer was washed with water and brine. The organic layer was then dried over Na2SO4 and concentrated. The crude product was purified by normal silica gel column chromatography (using 5% ethyl acetate in hexane) to get (1-phenyl-cyclohexyl)-acetonitrile (253) (2.4 g, 16.1%) as a colorless liquid.
Workup
- customAfter completion of the reaction
- extractionextracted with ethyl acetate
- washthe organic layer was washed with water and brine
- dry with materialThe organic layer was then dried over Na2SO4
- concentrationconcentrated
- customThe crude product was purified by normal silica gel column chromatography (using 5% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-902d03b0418445e6ad6dd44d2b73e479
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045486B2
Reaction notes
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