Diethyl Sulfate → 1-(2-Ethoxy-5-methylphenyl)ethanone

HRID 1712461Notes

Reaction equation

HRID 1712461 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[OH-].[Na+].S(OCC)(O[CH2:18][CH3:19])(=O)=O>C(O)C>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[CH3:19]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 150682-Hydroxy-5-methylacetophenone

Product 1

HCID 172450481-(2-Ethoxy-5-methylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The stirred solution of 20.0 g of 1-(2-hydroxy-5-methylphenyl)ethanone in 600 ml of ethanol is admixed with 8.0 g of sodium hydroxide. The resulting solution is admixed with 25.9 ml of diethyl sulphate and the mixture is kept at room temperature over 72 hours. The reaction mixture is concentrated by evaporation, and the residue is admixed with 1M NaOH (300 ml) and extracted with tert-butyl methyl ether (2×500 ml). The organic phases are washed with brine (300 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a brown solid from the residue by means of flash chromatography (SiO2 60F). Rt=4.49.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with tert-butyl methyl ether (2×500 ml)
  3. washThe organic phases are washed with brine (300 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7b956d85f6b64832b93c153daddb62bd
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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