Ethanol → Ethyl 3-(4-aminophenyl)acrylate

HRID 866746Notes

Reaction equation

HRID 866746 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH3:14].[OH-].[Na+]>O>[CH2:13]([O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:12][CH:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 929283-(4-Aminophenyl)prop-2-enoic acid

Product 1

HCID 97826Ethyl 3-(4-aminophenyl)acrylateYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

32.6 parts of 4-amino-cinnamic acid are heated under reflux for three hours in a mixture comprising 100 parts of absolute ethyl alcohol and 20 parts of 66°Be sulphuric acid. The product is poured on to 200 parts of water and 200 parts of ice, made alkaline to pH 8 by the addition of 38 parts of a 35° Be solution of sodium hydroxide, and the solid is filtered off, washed with water and recrystallised from 150 parts of ethyl alcohol and 150 parts of water. Ethyl-p-amino-cinnamate is thus obtained. Yield 78% M.p. 68°-69° C.

Workup

  1. temperatureunder reflux for three hours in a mixture
  2. filtrationthe solid is filtered off
  3. washwashed with water
  4. customrecrystallised from 150 parts of ethyl alcohol and 150 parts of water

Sources & evidence

ORD record
ord-22cd9268ef9c4fca9d88bf7663540418
Source dataset
uspto-grants-1978_07
Patent number
US04101543

Reaction notes

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