Chloroacetone → 1-[(4-Chlorophenyl)sulfanyl]propan-2-one

HRID 1084680Notes

Reaction equation

HRID 1084680 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1.[OH-].[Na+]>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:2][C:3](=[O:5])[CH3:4])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 7815p-ChlorothiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 3217461-[(4-Chlorophenyl)sulfanyl]propan-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Chloroacetone (32.3 g 0.347 mol) was added to a mixture of 4-chlorothiophenol (50 g. 0.347 mol) and sodium hydroxide (14 g, 0.347 mol) in water (400 ml) and the mixture was stirred at 25° C. for 1 hour. The mixture was extracted with ethyl ether and the organic phase was washed with water, dried with magnesium sulfate and concentrated to give 68 g (98%) of 1-[(4-chlorophenyl)-thio]-2-propanone.

Workup

  1. extractionThe mixture was extracted with ethyl ether
  2. washthe organic phase was washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b5752e6d49e46bcb6559c36daaea3a8
Source dataset
uspto-grants-1991_04
Patent number
US05006521

Reaction notes

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