Acetonitrile → 3-Hydroxy3, 3-di(4-biphenylyl) propionitrile

Reaktionsgleichung

[C:1]1([C:7]2[CH:26]=[CH:25][C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27](#[N:29])[CH3:28].[NH2-].[Na+]>C1C=CC=CC=1>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:26]=[CH:25][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)([OH:12])[CH2:28][C:27]#[N:29])=[CH:9][CH:8]=1

Komponenten

Versuchsvorschrift

To a stirred suspension of 4,4'-diphenylbenzophenone (15.5 g) and acetonitrile in dry benzene (200 mL), was added at a rapid dropwise rate a suspension of sodamide (2.3 g) in dry benzene (20 mL). The resulting mixture was stirred at reflux for 60 minutes, then the reaction was cooled and treated carefully with ice (50 g). The layers were separated, and the aqueous Phase was extracted with toluene. The organic extracts were washed with water, then were combined, dried (MgSO4) and evaporated to furnish 13.5 g of 3,3-bis[(1,1'-biphenyl)-4-yl]-3-hydroxypropanenitrile as an oil. The material was contained a minor impurity that was presumed to be the starting ketone.