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

HRID 2397243Notes

Reaction equation

HRID 2397243 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-8ab4942379eb4a5da801d42e493978be
Source dataset
uspto-grants-1977_05
Patent number
US04021440

Reaction notes

Loading…