Phenacyl bromide → Octanedioic acid methyl ester 2-oxo-2-phenylethyl ester

HRID 1039143Notes

Reaction equation

HRID 1039143 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][O:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>O.CO.CC(C)=O>[O:22]=[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([O:7][CH3:6])=[O:18]

Participants

7

Reactant 3

HCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 5541918-Methoxy-8-oxooctanoic acid

Product 1

HCID 59167744Octanedioic acid methyl ester 2-oxo-2-phenylethyl esterYield 90%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add a solution of sodium bicarbonate (2.12 g, 25.2 mmol) in water (10 mL) to a solution of suberic acid monomethyl ester (4.75 g, 25.2 mmol) in methanol (50 mL) at room temperature and stir the mixture for 30 minutes. Remove the solvent under reduced pressure and add the residue to a solution of 2-bromoacetophenone (5.0 g, 25.1 mmol) in acetone (150 mL) at room temperature under nitrogen. Heat the mixture at reflux for 10 hours and then remove the solvent under reduced pressure. Dilute the residue with diethyl ether (300 mL), stir for 20 minutes, filter through a short silica gel column, and wash with diethyl ether (2×50 mL). Remove the solvent under reduced pressure to provide octanedioic acid methyl ester 2-oxo-2-phenylethyl ester (6.9 g, 90%).

Workup

  1. customRemove the solvent under reduced pressure
  2. temperatureHeat the mixture
  3. temperatureat reflux for 10 hours
  4. customremove the solvent under reduced pressure
  5. additionDilute the residue with diethyl ether (300 mL)
  6. stirringstir for 20 minutes
  7. filtrationfilter through a short silica gel column
  8. washwash with diethyl ether (2×50 mL)
  9. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-357f9e67e4cb4b9f818e56e159471264
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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