Benzyl Chloride → 1-(3-(Phenylmethoxy)phenyl)ethan-1-one

HRID 2199008Notes

Reaction equation

HRID 2199008 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>CCOCC.CC(C)=O>[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 7503Benzyl Chloride2×HCID 8471TriethylamineHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate2×

Product 1

HCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mechanically stirred mixture of 1 kg. (7.35 mole) of 3-hydroxyacetophenone, 1.035 kg. (7.5 mole) anhydrous potassium carbonate and 0.945 kg. (7.5 mole) of benzylchloride in 4.1 of acetone was heated at reflux for 24 hours after which 0.1035 kg. (0.75 mole) portion of potassium carbonate and 0.0945 kg. (0.75 mole) portion of benzylchloride were added and refluxing continued. This addition was repeated after 72 hours of refluxing and refluxing continued for 96 hours. The reaction was cooled, filtered and the filtrate concentrated on a rotovapor. The filtrate was then treated with 0.202 kg. (2.0 mole) triethylamine and stirred overnight. The reaction was diluted with 1 liter ether and filtered. The filtrate was evaporated and the residue distilled to yield 1.429 kg. (86%) of the title compound as an oil.

Workup

  1. additionA mechanically stirred mixture of 1 kg
  2. temperatureat reflux for 24 hours after which 0.1035 kg
  3. temperaturerefluxing
  4. additionThis addition
  5. temperatureof refluxing
  6. temperaturerefluxing
  7. waitcontinued for 96 hours
  8. temperatureThe reaction was cooled
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated on a rotovapor
  11. additionThe filtrate was then treated with 0.202 kg
  12. filtrationfiltered
  13. customThe filtrate was evaporated
  14. distillationthe residue distilled
  15. customto yield 1.429 kg

Sources & evidence

ORD record
ord-a6c381e764b24bf0ad06411f1d51e9b6
Source dataset
uspto-grants-1982_11
Patent number
US04360700

Reaction notes

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