Acetonitrile → 3-Hydroxy-3-(4'-chloro-4-biphenylyl)-3-p-chlorophenylpropionitrile

HRID 1076085Notes

Reaction equation

HRID 1076085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[C:23](#[N:25])[CH3:24].[NH2-].[Na+]>C1C=CC=CC=1>[OH:9][C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:24][C:23]#[N:25]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24533Sodium amideHCID 203638444'-Chloro-4-biphenylyl 4-chlorophenyl ketone

Product 1

HCID 538313903-Hydroxy-3-(4'-chloro-4-biphenylyl)-3-p-chlorophenylpropionitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4'-Chloro-4-biphenylyl 4-chlorophenyl ketone (16.4 g.) and acetonitrile (2.25 g.) were reacted in benzene in the presence of sodamide (2.5 g.) by the method of Lettre and Wick (Annalen, 1957, 603, 194) to give 3-hydroxy-3-(4'-chloro-4-biphenylyl)-3-p-chlorophenylpropionitrile, m.p. 123°C after recrystallisation from benzene; λ max (ethanol) = 260 nm.

Sources & evidence

ORD record
ord-04b0fbbffc864ba38db4b678f9571588
Source dataset
uspto-grants-1976_05
Patent number
US03954869

Reaction notes

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