Potassium Formate → 2-Hydroxy-1-[4-(methylthio)phenyl]ethanone

HRID 361632Notes

Reaction equation

HRID 361632 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:14].[K+]>CO.CC(C)=O>[OH:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 2735122Potassium FormateHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

Product 1

HCID 620297022-Hydroxy-1-[4-(methylthio)phenyl]ethanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

119 g of 2-bromo-1-[4-methylthiophenyl]ethanone (prepared according to J. Amer. Chem. Soc., 1952, p. 5475) are dissolved in a mixture of 200 ml of methanol and 300 ml of acetone. 53 g of potassium formate are added and the mixture is heated under reflux for 4 hours. The organic solvents are evaporated, the residual oil is taken up with ethyl acetate and washed with a saturated solution of sodium chloride. The ethyl acetate is evaporated and the residual oil crystallises in isopropyl ether.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customThe organic solvents are evaporated
  4. washwashed with a saturated solution of sodium chloride
  5. customThe ethyl acetate is evaporated
  6. customthe residual oil crystallises in isopropyl ether

Sources & evidence

ORD record
ord-3a60839a458c433aa9fd54ab5f6f83f5
Source dataset
uspto-grants-1999_02
Patent number
US05866596

Reaction notes

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