Propionitrile → 3-(1-Cyanoethyl)benzoic acid

HRID 1759417Notes

Reaction equation

HRID 1759417 reaction equation
[C:1]([C:4]1[C:5]#[C:6][CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].ClC1C=CC=CC=1C(O)=O.[C:20](#[N:23])[CH2:21][CH3:22]>>[C:1]([C:4]1[CH:9]=[C:8]([CH:21]([CH3:22])[C:20]#[N:23])[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 7854PropionitrileHCID 83742-Chlorobenzoic AcidHCID 54434359HCID 54434359, compound

Product 1

HCID 983703-(1-Cyanoethyl)benzoic acid

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-f33b0d5b5f064925994c77f2bcdf7c08
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

Loading…