Ethyl Acrylate → Ethyl 3,4-dichlorocinnamate

HRID 1156474Notes

Reaction equation

HRID 1156474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=O.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=C.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC>C(OCC)(=O)C(OCC)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH:5]=[CH:13][C:12]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 14227TrioctylamineHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 53891084Ethyl 3,4-dichlorocinnamateYield 11.4%

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 7268Diethyl OxalateSolvent

Procedure

0.152 g (0.5 millimol) of bis-(acetylacetonato)palladium(II), 10.53 g (50 millimols) of 3,4-dichlorobenzoyl chloride, 7.5 g (75 millimols) of ethyl acrylate and 17.65 g (50 millimols) of tri-n-octylamine in 100 ml of diethyl oxalate are stirred for 2.5 hours at 120° C. The crude product is distilled in vacuo and then recrystallised from methanol. 1.4 g (11% of theory) of ethyl 3,4-dichlorocinnamate are obtained; melting point 56.0° C.

Workup

  1. distillationThe crude product is distilled in vacuo
  2. customrecrystallised from methanol

Sources & evidence

ORD record
ord-1f1d3da221234a7aa3c4c956d1a0a794
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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