Diketene → Butanoic acid, 3-oxo-, 2-phenoxyethyl ester

HRID 2290830Notes

Reaction equation

HRID 2290830 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[O:7]([CH2:14][CH2:15][OH:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:4]([O:16][CH2:15][CH2:14][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

3

Reactant 2

HCID 12661DiketeneHCID 31236Phenoxyethanol

Product 1

HCID 12237326Butanoic acid, 3-oxo-, 2-phenoxyethyl esterYield 40.8%

Conditions

Temperature
100 °C

Procedure

Diketene (84 g) was added dropwise with stirring to 140 g of 2-phenoxyethanol heated at 100° C. After the addition was completed, the reaction mixture was refluxed for an additional 22 hours. The reaction mixture was fractionally distilled to obtain 90.6 g of 2-phenoxyethyl acetoacetate, BP 140°-145° C./0.3 mm.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was refluxed for an additional 22 hours
  3. distillationThe reaction mixture was fractionally distilled

Sources & evidence

ORD record
ord-157efa50c7914e559e60e49929b9c163
Source dataset
uspto-grants-1986_10
Patent number
US04618678

Reaction notes

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