Benzoyl Peroxide → Methyl 2-[3-(methoxymethyl)phenyl]acetate

HRID 384136Notes

Reaction equation

HRID 384136 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12]Br)[CH:7]=1)C.BrN1[C:20](=[O:21])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CO.C[O-].[Na+].C(OCC)(=O)C>[CH3:1][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:21][CH3:20])[CH:7]=1

Participants

8

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10563066Ethyl 2-(3-(bromomethyl)phenyl)acetate

Product 1

HCID 131730198Methyl 2-[3-(methoxymethyl)phenyl]acetate

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolventHCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of ethyl(3-(bromomethyl)phenyl)acetate (1.78 g) in carbon tetrachloride (80 ml), 1.78 g of N-bromosuccinimide and 100 mg of benzoyl peroxide were added, and the reaction solution was heated overnight at reflux. The reaction solution was cooled, then the solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-10:90)) to afford a crude product. To a solution of the crude product (304 mg) in methanol (1 ml), 0.3 ml of sodium methoxide (25% methanol solution) was added, and the reaction solution was stirred at room temperature for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated aqueous ammonium chloride solution and a saturated saline solution sequentially, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., ethyl acetate/hexane (20:80)) to afford the title compound as a colorless oil.

Workup

  1. temperaturethe reaction solution was heated overnight
  2. temperatureat reflux
  3. temperatureThe reaction solution was cooled
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-10:90))
  7. customto afford a crude product
  8. washwashed with a saturated aqueous ammonium chloride solution
  9. dry with materiala saturated saline solution sequentially, and dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue obtained
  12. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., ethyl acetate/hexane (20:80))

Sources & evidence

ORD record
ord-3476a0159cb247b7aab78df3d7c82af5
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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