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

HRID 1763300Notes

Reaction equation

HRID 1763300 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-749b7fd915cd4e2e93d2d918a7e6f05c
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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