Ethanol → ethanone, 2-(methylthio)-1-phenyl-

HRID 399627Notes

Reaction equation

HRID 399627 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(O)C.[CH3:14][S-:15].[Na+]>O>[CH3:14][S:15][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 6259Phenacyl bromideHCID 4378561Sodium methanethiolate

Product 1

HCID 220651ethanone, 2-(methylthio)-1-phenyl-Yield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 21.4 g of bromoacetophenone is added to 90 ml of ethanol at 0° C., followed by slow addition of a solution of 5 g of sodium thiomethoxide in 25 ml of water. The reaction medium is stirred for one hour at 0° C. and then for 2 hours at room temperature, and is subsequently poured on to 500 ml of ice-water and extracted with twice 200 ml of ethyl ether. The ether phases are combined and washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulphate and then evaporated to dryness. The residue is distilled to give 2-(methylthio)acetophenone.

Workup

  1. waitfor 2 hours at room temperature
  2. extractionextracted with twice 200 ml of ethyl ether
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-25bbb6eb87ea4be780a3f08b72b6d6de
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

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