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

HRID 596672Notes

Reaction equation

HRID 596672 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. temperatureunder reflux for 28 hours
  2. customEvaporation of the filtered solution under reduced pressure

Sources & evidence

ORD record
ord-66e9476723614fbaafb54114f1466bcf
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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