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

HRID 460020

Reaction equation

HRID 460020 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:11][C:3]1[CH:4]=[CH:5][C:6]([C:8](=[O:9])[CH3:10])=[CH:7][C:2]=1[CH3:1])[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]-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-hydroxy-3-methylacetophenone (5.0 g) in dry acetonitrile (50 ml) was treated with potassium carbonate (5.06 g) and benzyl bromide (3.96 ml) and the reaction mixture heated at 40° C. After 3 hours the reaction was allowed to cool and was concentrated. The residue was partitioned between water and ethyl acetate; the aqueous layer separated and extracted twice more with ethyl acetate. The organic solutions were combined and were dried with brine and over magnesium sulfate and concentrated to give the title compound as a colourless oil

Workup

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customThe residue was partitioned between water and ethyl acetate
  4. customthe aqueous layer separated
  5. extractionextracted twice more with ethyl acetate
  6. dry with materialwere dried with brine and over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da235d1cfd0447f28bdf62d1f7e867b5
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Linked notes

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