Chloroacetone → HCID 11109189, compound

HRID 1700627Notes

Reaction equation

HRID 1700627 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[C:10]([SH:15])[CH2:9]1.Cl[CH2:17][C:18](=[O:20])[CH3:19].[O-]CC.[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[C:10]([S:15][CH2:17][C:18](=[O:20])[CH3:19])[CH2:9]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 2723922Sodium ethoxideHCID 11118132HCID 11118132, compound

Product 1

HCID 11109189HCID 11109189, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 5-(2-chlorophenyl)-3-mercapto-2-cyclohexen-1-one (1.8 g) and chloroacetone (0.7 g) in ethanol (20 ml) was added a solution of 20% sodium ethoxide in ethanol (0.48 g), and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, and to the residue was ethyl acetate. The mixture was subjected to extraction, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give 5-(2-chlorophenyl)-3-(2-oxopropylthio)-2-cyclohexen-1-one (2.3 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionThe mixture was subjected to extraction
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f968d3dce3a4174a6da2b85f7f770fb
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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