Ethanol → Ethyl 2-hydroxy-γ-oxobenzenebutanoate

HRID 1283398Notes

Reaction equation

HRID 1283398 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5].S(=O)(=O)(O)O.C(Cl)(Cl)Cl.[CH2:24](O)[CH3:25]>>[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([O:10][CH2:24][CH3:25])=[O:9])=[O:5]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 30160863-(2-Hydroxybenzoyl)propionic acid

Product 1

HCID 20352582Ethyl 2-hydroxy-γ-oxobenzenebutanoate

Procedure

A solution of 3-(o-hydroxybenzoyl)propionic acid (18.8 g.) in ethanol (120 ml.) was treated with concentrated sulphuric acid (1 ml.) and the mixture heated at reflux temperature for 12 hours. It was cooled, poured into ice-water (350 ml.) and the oily solid isolated with chloroform. It (18.6 g.) was purified by distillation at reduced pressure and had bp 112°-113°C at 0.1 mm; nD24.5 = 1.5301.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 12 hours
  3. temperatureIt was cooled
  4. distillationIt (18.6 g.) was purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-313842a6099446cea8d8545d92571aaa
Source dataset
uspto-grants-1976_08
Patent number
US03975388

Reaction notes

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