M-Cresol → 1-(3-methylphenoxy)propan-2-one

HRID 1288231Notes

Reaction equation

HRID 1288231 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[I-].[K+].[CH3:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O.O>[CH3:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:2][C:3](=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 342M-CresolHCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

Product 1

HCID 3095751-(3-methylphenoxy)propan-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A mixture of chloroacetone (43.75 g.) and finely-powdered potassium iodide (1 g.) in ethyl methyl ketone (50 ml.) was added dropwise, over 25 minutes, to a stirred, refluxing mixture of 3-methylphenol (54 g.) and dry potassium carbonate (82 g.) in ethyl methyl ketone (100 ml). Stirring and refluxing were continued for a total of 5 hours and the mixture was cooled, poured into water (cs. 500 ml.) and extracted with ether. The ether extract was washed exhaustively with 5N-sodium hydroxide, dried over anhydrous sodium sulphate and evaporated. The residue was distilled to give a fraction b.p. 126°-134°/13 mm. Redistillation gave 1-(3-methylphenoxy)-propan-2-one, b.p. 124°-126°/13 mm.

Workup

  1. additionwas added dropwise, over 25 minutes, to a stirred
  2. temperaturerefluxing
  3. temperaturerefluxing
  4. customwere continued for a total of 5 hours
  5. temperaturethe mixture was cooled
  6. extractionextracted with ether
  7. extractionThe ether extract
  8. washwas washed exhaustively with 5N-sodium hydroxide
  9. dry with materialdried over anhydrous sodium sulphate
  10. customevaporated
  11. distillationThe residue was distilled
  12. customto give a fraction b.p. 126°-134°/13 mm
  13. distillationRedistillation

Sources & evidence

ORD record
ord-665edb7e90c14f58a462a2a1e9b8d7b5
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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