4-Methylbenzenethiol → 1-Acetoxy-3-(4-methylphenylthio)acetone

HRID 571614

Reaction equation

HRID 571614 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH2:8]Cl)=[O:7])(=[O:3])[CH3:2].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C(N(CC)CC)C>COC(C)(C)C>[C:1]([O:4][CH2:5][C:6]([CH2:8][S:17][C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 8471TriethylamineHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-

Product 1

HCID 682846161-Acetoxy-3-(4-methylphenylthio)acetoneYield 97.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 1-acetoxy-3-chloroacetone (5.0 g, 33.2 mmol) and 4-methylthiophenol (4.12 g, 33.2 mmol) in tert-butyl methyl ether (100 ml) was slowly added triethylamine (5.1 ml, 36.6 mmol) under ice-cooling. The solution was stirred at room temperature for 30 minutes. The reaction solution was washed with water, saturated aqueous sodium hydrogen carbonate solution, then saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to give 7.72 g of 1-acetoxy-3-(4-methylphenylthio)acetone (yield: 97%) as oil.

Workup

  1. temperaturecooling
  2. washThe reaction solution was washed with water, saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-0358b8ce5dcc4b9b830d8276f3ec09a8
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Linked notes

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