Thionyl Chloride → 2-(3-Benzoylphenyl)propanenitrile

HRID 1759418Notes

Reaction equation

HRID 1759418 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.ClC([C:17]1[CH:18]=[C:19](C(C)C#N)[CH:20]=[CH:21][CH:22]=1)=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 983703-(1-Cyanoethyl)benzoic acidHCID 30163933-(1-Cyanoethyl)benzoyl chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 393252-(3-Benzoylphenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Carboxybenzyne prepared from 2-chlorobenzoic acid in the presence of a strong base is reacted with propionitrile to produce alpha-(m-carboxyphenyl)propionitrile (R. Biehl et al., J. Org. Chem., 31, 602 (1966)). The alpha-(m-carboxyphenyl)propionitrile is converted to alpha-(m-chlorocarbonylphenyl)propionitrile by using thionyl chloride. Friedel-Crafts reaction of alpha-(m-chlorocarbonylphenyl)propionitrile with benzene using aluminum chloride affords alpha-(m-benzoylphenyl)propionitrile. Hydrolysis of the alpha-(m-benzoylphenyl)propionitrile with methanol/sodium hydroxide gives alpha-(m-benzoylphenyl)propionic acid (see British Pat. No. 1,360,560).

Sources & evidence

ORD record
ord-e170c49cff9340f193c46307c6f8489e
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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