Diphenylacetonitrile → HCID 54757233, compound
Reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH:19]=[CH2:20]>C(O)(C)(C)C.CO>[C:8]([C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:20][CH2:19][C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])#[N:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A suspension of diphenylacetonitrile (38.6 g, 200 mmol) in tert-butanol (200 ml) was warmed to 60° C. for 30 minutes. The resulting solution was cooled to 50° C. and a solution of potassium hydroxide (0.6 g, 10.69 mmol) in methanol (2 mL) was added. tert-Butyl acrylate (30 mL, 200 mmol) was then added dropwise and the mixture was stirred at 50° C. for 2 hours and at room temperature for 18 hours. Further potassium hydroxide (0.6 g, 10.69 mmol) was added and the mixture was re-warmed to 50° C. for 3 hours. The reaction mixture was then concentrated in vacuo and the residue was diluted with diethyl ether (300 mL), washed with water (200 mL), dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 90% yield, 57.95 g.
Workup
- temperatureThe resulting solution was cooled to 50° C.
- temperaturethe mixture was re-warmed to 50° C. for 3 hours
- concentrationThe reaction mixture was then concentrated in vacuo
- additionthe residue was diluted with diethyl ether (300 mL)
- washwashed with water (200 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-26d938eba02549f4afecabb23805f751
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268881B2
Reaction notes
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