Water → Ethyl 2-(3-acetamido-4-hydroxyphenyl)propionate

HRID 1658152Notes

Reaction equation

HRID 1658152 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[C:16](OC(=O)C)(=[O:18])[CH3:17].O>N1C=CC=CC=1>[C:16]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 12202638Ethyl 3-amino-4-hydroxy-phenyl-propionate

Product 1

HCID 20358686Ethyl 2-(3-acetamido-4-hydroxyphenyl)propionateYield 65.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of ethyl 2-(3-amino-4-hydroxyphenyl)propionate (10.46 g.) and acetic anhydride (5.6 g.) in dry pyridine (50 ml.) was heated on a steam bath for 1.25 hours. The reaction mixture was poured into water (500 ml.), precipitating an oil. On cooling the oil solidified. The solid was removed by filtration and washed with water. After drying, ethyl 2-(3-acetamido-4-hydroxyphenyl)propionate (8.25 g.) was obtained, m.p. 137°-141°C.

Workup

  1. customprecipitating an oil
  2. temperatureOn cooling the oil
  3. customThe solid was removed by filtration
  4. washwashed with water
  5. customAfter drying

Sources & evidence

ORD record
ord-3be54a4bd55e4905984dfa98796b5857
Source dataset
uspto-grants-1976_06
Patent number
US03962452

Reaction notes

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