Diethyl Ether → Ethyl 3-(4-acetamidophenyl)prop-2-enoate

HRID 2057647Notes

Reaction equation

HRID 2057647 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH2:15]([O:17]CC)[CH3:16].C(OC(=O)C)(=O)C>CCCCCC>[C:15]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 7918Acetic AnhydrideHCID 97826Ethyl 3-(4-aminophenyl)acrylate

Product 1

HCID 53715054Ethyl 3-(4-acetamidophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A sample of 50 g. of ethyl p-aminocinnamate is dissolved in 500 ml. of ethyl ether and a solution of 28 g. of acetic anhydride in 30 ml. of ether is added dropwise. When the addition is complete, the reaction is allowed to stir for another hour. The mixture is then diluted with hexane and filtered, providing ethyl p-acetamidocinnamate.

Workup

  1. additionWhen the addition
  2. filtrationfiltered

Sources & evidence

ORD record
ord-aef76b387ecd40e789ba34060c8ff656
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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