Potassium Carbonate → Methyl 3-[2-(2,3-epoxypropoxy)benzoyl]propionate

HRID 1579263Notes

Reaction equation

HRID 1579263 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:22]([CH:24]1[O:26][CH2:25]1)Br>CC(CC)=O>[O:26]1[CH2:25][CH:24]1[CH2:22][O:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 13530371HCID 13530371, compound

Product 1

HCID 13530373Methyl 3-[2-(2,3-epoxypropoxy)benzoyl]propionateYield 104.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A well stirred mixture of methyl 3-(2-hydroxybenzoyl)propionate (63.3 g, 0.3 mole), potassium carbonate (48.4 g, 0.35 mole), epibromohydrin (117 ml, 1.4 mole), and dry ethyl methyl ketone (2000 ml) was heated under reflux for 28 hours. Evaporation of the filtered solution under reduced pressure gave methyl 3-[2-(2,3-epoxypropoxy)benzoyl]propionate (83 g, 100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 28 hours
  3. customEvaporation of the filtered solution under reduced pressure

Sources & evidence

ORD record
ord-36e66655dc874d30af95c11c6c403471
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

Loading…