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

HRID 2167835

Reaction equation

HRID 2167835 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-eee07cea7e334acc82d58ad89ec6569c
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Linked notes

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