Acetyl chloride → 1-(4-(Methylthio)phenyl)ethan-1-one

HRID 1064

Reaction equation

HRID 1064 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([S:11][CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:13](Cl)(=[O:15])[CH3:14]>C(Cl)Cl>[CH3:14][C:13]([C:8]1[CH:9]=[CH:10][C:5]([S:11][CH3:12])=[CH:6][CH:7]=1)=[O:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7520ThioanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 745011-(4-(Methylthio)phenyl)ethan-1-oneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

123 g (0.92 mol) of AlCl3 are added with a spatula to a mixture of 100 g (0.8 mol) of thioanisole, 750 ml of CH2Cl2 and 63 ml (0.9 mol) of acetyl chloride, cooled to 0° C. beforehand, said addition being carried out so that the temperature does not exceed 10° C. The mixture is stirred for 1 h at room temperature, heated for 1 h at 40° C. and then poured into 800 ml of an ice/water mixture. The resulting mixture is separated and extracted with CH2Cl2. The organic phases are combined, washed with water and then dried over MgSO4 and concentrated to give 117.1 g of 4-(methylthio)acetophenone.

Workup

  1. additionaddition
  2. customdoes not exceed 10° C
  3. temperatureheated for 1 h at 40° C.
  4. customThe resulting mixture is separated
  5. extractionextracted with CH2Cl2
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b9e829672ee641d4912a1f2c034f3d35
Source dataset
uspto-grants-1998_03
Patent number
US05723485

Linked notes

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