Phenol → 2-(4-Chlorophenoxy)-1-phenylethanone

HRID 1449337Notes

Reaction equation

HRID 1449337 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1C(C(CBr)=O)=[CH:12][CH:11]=[C:10]([Cl:18])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([CH2:28][O:29]C)[O:26][CH3:27]>>[Cl:18][C:10]1[CH:11]=[CH:12][C:27]([O:26][CH2:25][C:28]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:29])=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 3095712-(4-Chlorophenoxy)-1-phenylethanone

Procedure

A mixture of 40.5 g. (0.43 mole) of phenol, 100 g. (0.428 mole) of 4-chloro-α-bromoacetophenone, 100 g. (0.725 mole) of potassium carbonate and 500 ml. of glyme is heated to its reflux temperature and maintained at reflux for about 6 hours. The reaction mixture is evaporated to remove the solvent. The residue is diluted with water and diethyl ether, and the layers are separated. The ether layer is washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The ether solution is evaporated to provide a dark oil which gradually solidifies on cooling. The solid is recrystallized from ethanol to provide 4-chloro-α-phenoxyacetophenone, m.p. 81°-86° C.

Workup

  1. additionA mixture of 40.5 g
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for about 6 hours
  5. customThe reaction mixture is evaporated
  6. customto remove the solvent
  7. additionThe residue is diluted with water and diethyl ether
  8. customthe layers are separated
  9. washThe ether layer is washed with water and saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customThe ether solution is evaporated
  12. customto provide a dark oil which
  13. temperatureon cooling
  14. customThe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-5b4ec59682de4894a6330fcc9c134d4c
Source dataset
uspto-grants-1980_02
Patent number
US04190590

Reaction notes

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