Benzyl Bromide → Ethanone, 1-[3-methyl-4-(phenylmethoxy)phenyl]-

HRID 920524

Reaction equation

HRID 920524 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 12969325Ethanone, 1-[3-methyl-4-(phenylmethoxy)phenyl]-Yield 99.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4′-hydroxy-3′-methylacetophenone (10.00 g; 66.6 mmol) and K2CO3 (13.80 g; 99.9 mmol) in acetone (100 mL) was stirred, at RT for 40 minutes. Subsequently, benzyl bromide (7.9 mL; 66.6 mmol) was added and the resulting mixture was heated under reflux for 2.5 h. After cooling to RT the mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with 5% aqueous ammonia, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 1-(4-benzyloxy-3-methylphenyl)-ethanone (15.86 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. temperatureAfter cooling to RT the mixture
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with 5% aqueous ammonia, water, and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a70cc3c54f4465b9e8c3febbea89ff0
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Linked notes

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