Acrylonitrile → HCID 21274853, compound

HRID 570066Notes

Reaction equation

HRID 570066 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10](#[N:13])[CH:11]=[CH2:12].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:12][CH2:11][C:10]#[N:13])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 113352,6-DimethylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21274853HCID 21274853, compound

Procedure

In a modification of this Friedel-Crafts reaction, 2,6-di-methylphenol is treated with acrylonitrile in the presence of aluminum chloride to yield 3-(3,5-dimethyl-4-hydroxyphenyl)propionitrile. Upon hydrolysis of this and esterification of the resulting free acid with methanol and p-toluenesulfonic acid, there is obtained methyl 3-(3,5-dimethyl-4-hydroxyphenyl)propionate, M.P. 70°-83° C.

Sources & evidence

ORD record
ord-70308dcf48b943d891670d17df574d2d
Source dataset
uspto-grants-1988_03
Patent number
US04734519

Reaction notes

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