Dimethyl Sulfate → 2-Methoxy-1-phenylethanone

HRID 1707758Notes

Reaction equation

HRID 1707758 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH-].[K+].[OH:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>O>[CH3:5][O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 776982-Methoxy-1-phenylethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

250 g (1.98 mol) of dimethyl sulfate is added dropwise to a mixture of 130 g of potassium hydroxide in 1.1 of water and 260 g (1.90 mol) of 2-hydroxyacetophenone with cooling and vigorous stirring in such a way that the reaction solution is not heated above 40° C. After the reaction temperature has then been kept at 80° C. for 30 minutes, the mixture is allowed to cool to room temperature and extracted by shaking with a total of 250 ml of chloroform. The organic phase is shaken three times with 100 ml of 2N sodium hydroxide solution each time and dried over sodium sulfate. After filtration and removal of the solvent on a rotary evaporator, the oil obtained is distilled in vacuo.

Workup

  1. temperaturewith cooling
  2. temperatureis not heated above 40° C
  3. extractionextracted
  4. stirringby shaking with a total of 250 ml of chloroform
  5. stirringThe organic phase is shaken three times with 100 ml of 2N sodium hydroxide solution each time
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration and removal of the solvent
  8. customon a rotary evaporator
  9. customthe oil obtained
  10. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-ae7620afa84b4d1eb2aa1fda39b750da
Source dataset
uspto-grants-1994_10
Patent number
US05354869

Reaction notes

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