Ethanol → Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl ester

HRID 1413046Notes

Reaction equation

HRID 1413046 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:14](O)[CH3:15].S(=O)(=O)(O)O>C(Cl)CCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:11])[C:8]([O:10][CH2:14][CH3:15])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1011822-(4-Hydroxy-phenoxy)-propionic acid

Product 1

HCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-(4-hydroxyphenoxy)propionic acid (9.0 g), ethanol (15 ml) and concentrated sulfuric acid (0.5 ml) were added to ethylene dichloride (40 ml) and the mixture was heated under reflux overnight. The reaction mixture was cooled to room temperature and the ethylene dichloride layer was separated and washed twice with water and twice with aqueous 2% NaHCO3. The organic fraction was dried over sodium sulfate and the solvent was removed by distillation under reduced pressure to give the product, ethyl 2-(4-hydroxyphenoxy)-propionate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe ethylene dichloride layer was separated
  4. washwashed twice with water and twice with aqueous 2% NaHCO3
  5. dry with materialThe organic fraction was dried over sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-54b6d373155a409f83d85d4cb63729ce
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

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