Water → (4-Methylphenylthio)acetone

HRID 589667Notes

Reaction equation

HRID 589667 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].C([O-])(O)=O.[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.O>CN(C=O)C>[C:12]1([CH3:11])[CH:17]=[CH:16][C:15]([S:18][CH2:2][C:3](=[O:5])[CH3:4])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 78114-MethylbenzenethiolHCID 516892Sodium Bicarbonate

Product 1

HCID 2779874(4-Methylphenylthio)acetoneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Chloroacetone (11.6 g, 125 mmol) and NaHCO3 (12.6 g, 150 mmol) were added to a solution of 4-methylthiophenol (10 g, 80.5 mmol) in dry DMF (50 mL). The mixture was stirred at 50-60° C. for 1 h. The cooled reaction mixture was poured into water (200 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried with K2CO3, evaporated to dryness and the residue was distilled (b.p. 145-148° C./12 mm) to give 11.7 g of 1-(p-tolyl sulfanyl)propan-2-one (81%).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic extracts were dried with K2CO3
  4. customevaporated to dryness
  5. distillationthe residue was distilled (b.p. 145-148° C./12 mm)

Sources & evidence

ORD record
ord-32e120e285da46fbbf690c4241753682
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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