Propionitrile → 3-(1-Cyanoethyl)benzoic acid

反応式

[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]

参加物

反応物 3

HCID 7854Propionitrile

HCID 83742-Chlorobenzoic Acid

HCID 54434359HCID 54434359、化合物

生成物 1

HCID 983703-(1-Cyanoethyl)benzoic acid

実験手順

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).

出典と根拠

ORDレコード: ord-f33b0d5b5f064925994c77f2bcdf7c08
出典データセット: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04340740

反応ノート

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