4'-Hydroxyacetophenone → HCID 21704960, compound

HRID 1595510Notes

Reaction equation

HRID 1595510 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.CS(O[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:28][S:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:19][CH:20]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethane

Product 1

HCID 21704960HCID 21704960, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.6 g (0.1 mole) p-hydroxyacetophenone, 29.4 g (0.1 mole) 4-(methylsulfonyloxy)phenethyl methanesulfonate and 42.4 g (0.3 mole) potassium carbonate in acetonitrile were refluxed over night. The salts were filtered off and the solvent was evaporated in vacuo. The residue was crystallized in isopropyl alcohol. The crystals were dissolved in dichloromethane, washed with diluted potassium carbonate, dried (magnesium sulfate), filtered and evaporated to give 22.7 g (yield 68%) 4-[2-(4-acetylphenoxy)ethyl]phenyl methanesulfonate.

Workup

  1. filtrationThe salts were filtered off
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was crystallized in isopropyl alcohol
  4. dissolutionThe crystals were dissolved in dichloromethane
  5. washwashed with diluted potassium carbonate
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4b9ee6a3f76c4e9cb301915470846992
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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