m-Chloroperbenzoic acid → HCID 14957692, compound

HRID 327137Notes

Reaction equation

HRID 327137 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:13])[CH:11]2[O:22][CH:10]2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1459344716020-15-8

Product 1

HCID 14957692HCID 14957692, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3 g (17.4 mmol) of 2,2-dimethyl-1-oxo-1,2-dihydronaphthalene (L. H. Klemm, J. Shabtai, D. R. Taylor, J. Org. Chem., 1968, 33, 1480) in 30 mL of CH2Cl2, were added 6.00 g (19.1 mmol) of m-chloroperbenzoic acid dissolved in 90 mL CH2Cl2 and the resulting mixture was stirred overnight at room temperature. The resulting solution was washed succesively with Na2S2O5 and NaHCO3 solutions and dried over MgSO4. The solvent was removed to yield 3.27 g of a crude that was chromatographed on silica gel eluting with hexane-CH2Cl2 mixtures of increasing polarity. 2.09 g of the title compound of this preparation were obtained as a colorless oil (yield: 64%).

Workup

  1. washThe resulting solution was washed succesively with Na2S2O5 and NaHCO3 solutions
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed
  4. customto yield 3.27 g of a crude that
  5. customwas chromatographed on silica gel eluting with hexane-CH2Cl2 mixtures
  6. temperatureof increasing polarity

Sources & evidence

ORD record
ord-5154fdf2121a4b8e98235dd6e953a9f0
Source dataset
uspto-grants-1993_12
Patent number
US05272170

Reaction notes

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