Ethanol → Ethyl 2-hydroxy-γ-oxobenzenebutanoate

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

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 6212Chloroform

HCID 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.