Benzoyl chloride → Ethyl 3-phenylprop-2-enoate

HRID 1156470Notes

Reaction equation

HRID 1156470 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=C.C(N(CCCC)CCCC)CCC>CC1C=CC(C)=CC=1>[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7622TributylamineHCID 8821Ethyl Acrylate

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoateYield 86%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

0.095 g (2.5×10-4 mols) of diacetato-bipyridylpalladium(II), 2.88 ml (25 millimols) of benzoyl chloride, 3.39 ml (31.25 millimols) of ethyl acrylate and 5.96 ml (25 millimols) of tri-n-butylamine in 50 ml of p-xylene, are stirred for 3 hours at 120° C. Working up as described in the preceding examples affords 3.78 g (86% of theory) of ethyl cinnamate.

Sources & evidence

ORD record
ord-9f7bf4e37aaf4f17ad424defc2fa6bdd
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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