Chloroacetone → HCID 20484445, compound

HRID 648062Notes

Reaction equation

HRID 648062 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][O:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:16])=[O:15])[C:11]([CH3:17])=[CH:10][C:9]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].ClCC(=O)C.[I-].[K+]>CC(C)=O.[I-].[K+]>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:16])=[O:15])[C:11]([CH3:17])=[CH:10][C:9]=1[O:18][CH2:2][C:3](=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium Carbonate2×HCID 12811402HCID 12811402, compoundHCID 86739088HCID 86739088, compound

Product 1

HCID 20484445HCID 20484445, compound

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent2×

Procedure

Potassium iodide (0.075 g) was added to a stirred solution of chloroacetone (3 ml) in dry acetone (3.5 ml) and the mixture was stirred for 16 hours. 2-Methoxy-5-methyl-4-methylsulphinylphenol (5.0 g) and potassium carbonate (0.85 g) were heated at reflux with stirring in dry acetone (25 ml). The chloroacetone/potassium iodide solution and potassium carbonate (3.4 g) were then added in four equal portions over 2 hours. The mixture was heated at reflux for a further 2 hours, cooled and filtered, the filter cake being washed well with acetone. The acetone was removed under reduced pressure and the residue chromatographed on a column of silica gel eluting with methylene chloride/methanol mixtures (gradient I to 3% v/v methanol). Trituration with diethyl ether gave the ketone (4.6 g) as colourless crystals, m.p. 104°-106°.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was heated
  3. temperatureat reflux for a further 2 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washthe filter cake being washed well with acetone
  7. customThe acetone was removed under reduced pressure
  8. customthe residue chromatographed on a column of silica gel eluting with methylene chloride/methanol mixtures (gradient I to 3% v/v methanol)

Sources & evidence

ORD record
ord-63efcc6a2b6b40e595d0c33c18d4cc64
Source dataset
uspto-grants-1983_10
Patent number
US04410548

Reaction notes

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