Phenolphthalein → Acetonitrile, [[4-(1,1-dimethylethyl)phenyl]thio]-
Reaction equation
C1(S)C=CC=CC=1.Cl[CH2:9][C:10]#[N:11].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1>[OH-].[Na+].C(O)C.O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([S:22][CH2:9][C:10]#[N:11])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]Participants
Procedure
The substituted phenylthioacetonitrile starting materials can be prepared by the reaction of the corresponding thiophenol with chloroacetonitrile in alcoholic sodium hydroxide. In a representative procedure, a solution of 100 grams of 4-tert-butylthiophenol and 45.3 grams chloroacetonitrile in 225 milliliters of 95 percent ethanol is stirred at room temperature while a solution of 24 grams sodium hydroxide in 36 milliliters water is added dropwise until the mixture remains alkaline to phenolphthalein. Slight spontaneous warming occurs during the addition. The mixture is then diluted with an equal volume of water and extracted twice with ether. The ether extract is washed with water, dried over sodium sulfate, and distilled, yielding the 2-(4-tert-butylphenylthio)acetonitrile as a liquid boiling at 153°-6° C. under a pressure of 4 millimeters of mercury.
Workup
- additionis added dropwise until the mixture
- temperatureSlight spontaneous warming
- additionoccurs during the addition
- extractionextracted twice with ether
- extractionThe ether extract
- washis washed with water
- dry with materialdried over sodium sulfate
- distillationdistilled
Sources & evidence
- ORD record
- ord-fdf1cc8152bc4ff8b03d2bb123f50d7f
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03994976
Reaction notes
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