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

HRID 972761Notes

Reaction equation

HRID 972761 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%). (Found: M+, 264; C14H16O5 requires M, 264).

Workup

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

Sources & evidence

ORD record
ord-bb43c9ce74d544e68861a7e8b3346f72
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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