Ethyl Acrylate → HCID 3346402, compound

HRID 1156475Notes

Reaction equation

HRID 1156475 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](Cl)=O.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=C.C(N(C(C)C)C(C)C)C>C(#N)C1C=CC=CC=1.[Pd](C#N)C#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[CH:6]=[CH:15][C:14]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 81531DiisopropylethylamineHCID 870033,5-Dimethoxybenzoyl chloride

Product 1

HCID 3346402HCID 3346402, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 178514132HCID 178514132, compoundCatalystHCID 7505BenzonitrileSolvent

Procedure

0.0792 g (5 millimols) of palladium(II) cyanide, 10.03 g (50 millimols) of 3,5-dimethoxybenzoyl chloride, 6.26 g (62.5 millimols) of ethyl acrylate and 6.46 g (50 millimols) of N-ethyldiisopropylamine, in 100 ml of benzonitrile, are stirred for 70 minutes at 140° C. The crude product is distilled in vacuo. Working up affords 5.83 g (49% of theory) of ethyl 3,5-dimethoxycinnamate as a colourless liquid.

Workup

  1. distillationThe crude product is distilled in vacuo

Sources & evidence

ORD record
ord-83097b7052414567906a93f5e23dff74
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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