Acrylic Acid → p-Cyanocinnamic acid

HRID 484078Notes

Reaction equation

HRID 484078 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:12]=[CH:11][C:10]([OH:14])=[O:13])=[CH:3][CH:4]=1)#[N:7]

Participants

3

Reactant 2

HCID 6581Acrylic AcidHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 86773p-Cyanocinnamic acidYield 78.6%

Procedure

A Heck reaction of 4-bromobenzonitrile and acrylic acid gave 4-cyanocinnamic acid. The acid was reduced to the corresponding alcohol with ethyl chloroformate and then sodium borohydride. Yield 78.6%

Sources & evidence

ORD record
ord-dc94752bce6c406a9b44b5f7de706f09
Source dataset
uspto-grants-1993_07
Patent number
US05229400

Reaction notes

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