Acetonitrile → Ethanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-1-(2-naphthalenyl)-

HRID 733113Notes

Reaction equation

HRID 733113 reaction equation
C(#N)C.[CH3:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6].OI(C1C=CC=CC=1)[O:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(OCC)(=O)C>[S:20]([O:22][CH2:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6])([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:21])=[O:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 71222-AcetylnaphthaleneHCID 325434[Hydroxy(tosyloxy)iodo]benzene

Product 1

HCID 10783345Ethanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-1-(2-naphthalenyl)-Yield 68.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetonitrile solution (40 mL) containing 2-acetonaphthone (1.70 g, 9.99 mmol) and [hydroxyl(tosyloxy)iodo]benzene (4.00 mg, 10.2 mmol) was heated under reflux for 3 hours. The reaction mixture was cooled, and ethyl acetate was added thereto. The reaction solution was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove the solvent to obtain the title compound (2.33 g, 68.5%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe reaction solution was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto remove the solvent

Sources & evidence

ORD record
ord-df93b800435f48b884e1d81f2190d520
Source dataset
uspto-grants-2009_09
Patent number
US07589096B2

Reaction notes

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