4'-Hydroxyacetophenone → 1-[4-(Benzyloxy)phenyl]ethan-1-one

HRID 2374770Notes

Reaction equation

HRID 2374770 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)=[O:17]>CC(C)=O.C(OCC)(=O)C>[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
19 °C

Procedure

14.5 cm3 of benzyl bromide and 16.75 g of potassium carbonate were added, at a temperature in the region of 19° C., to 15 g of 4-hydroxyacetophenone dissolved in 180 cm3 of acetone. The reaction medium was heated and maintained at the reflux temperature of the acetone for 4 hours. After cooling to a temperature in the region of 19° C., the reaction medium was suction-filtered through a sinter funnel and the insoluble material was rinsed again with 10 cm3 of acetone. The organic phase was evaporated under reduced pressure (2 kPa; 45° C.) and the solid obtained was dissolved in 300 cm3 of ethyl acetate. The organic solution was washed with twice 100 cm3 of water and then with 100 cm3 of saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered through a sinter funnel and then evaporated under reduced pressure (2 kPa; 45° C.). The solid residue was triturated in 20 cm3 of pentane, suction-filtered through a sinter funnel and oven-dried under reduced pressure (10 kPa; 20° C.). 23.1 g of 4-benzyloxyacetophenone were obtained in the form of a white solid melting at 99° C.

Workup

  1. temperatureThe reaction medium was heated
  2. filtrationthe reaction medium was suction-filtered through a sinter funnel
  3. washthe insoluble material was rinsed again with 10 cm3 of acetone
  4. customThe organic phase was evaporated under reduced pressure (2 kPa; 45° C.)
  5. customthe solid obtained
  6. washThe organic solution was washed with twice 100 cm3 of water
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered through a sinter funnel
  9. customevaporated under reduced pressure (2 kPa; 45° C.)
  10. customThe solid residue was triturated in 20 cm3 of pentane
  11. filtrationsuction-filtered through a sinter funnel
  12. customoven-dried under reduced pressure (10 kPa; 20° C.)

Sources & evidence

ORD record
ord-4c89a9e700ab42649b55b79d776f11c3
Source dataset
uspto-grants-2008_12
Patent number
US07462613B2

Reaction notes

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