Potassium Carbonate → HCID 69484304, compound

HRID 1374074Notes

Reaction equation

HRID 1374074 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-:14].[K+].[K+].[CH2:19]([O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br)[CH3:20]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:14][CH2:25][CH2:24][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:27])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 78066(+-)-Methyl mandelate

Product 1

HCID 69484304HCID 69484304, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g (60.2 mmol) of hydroxyphenylacetic acid methyl ester (Aldrich) is dissolved in 75 ml of acetone. 18.4 g (133 mmol) of solid potassium carbonate is added. 17.8 ml (123 mmol) of 4-bromobutyric acid ethyl ester is added in drops under reflux within 15 minutes, and it is kept at this temperature for another 4 hours and stirred overnight at room temperature. Precipitate is filtered out, the solution is evaporated to the dry state, and it is chromatographed on silica gel (hexane/ethyl acetate 3:1). The fractions that contain the product are combined and concentrated by evaporation.

Workup

  1. temperatureunder reflux within 15 minutes
  2. filtrationPrecipitate is filtered out
  3. customthe solution is evaporated to the dry state, and it
  4. customis chromatographed on silica gel (hexane/ethyl acetate 3:1)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-095c9eade1a44d22962be956b4c30313
Source dataset
uspto-grants-2007_01
Patent number
US07164016B2

Reaction notes

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