m-Chloroperbenzoic acid → HCID 86668656, compound

HRID 73626Notes

Reaction equation

HRID 73626 reaction equation
[CH2:1]1[CH:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[CH:4][CH2:3][O:2]1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)Cl>[O:19]1[C:5]23[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:1][O:2][CH2:3][CH:4]13

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66582146HCID 66582146, compound

Product 1

HCID 86668656HCID 86668656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,5,6,7,8,8a-hexahydro-1H-isochromene (0.410 g, 2.97 mmol) in CH2Cl2 (10 mL) at 0° C. was added MCPBA (˜77%, 1.24 g, 445 mmol). The mixture was stirred at rt for 3 hr. It was quenched with sated aq. sodium sulfite. The mixture was diluted with CH2Cl2 and sat'd. aq. NaHCO3 then extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound.

Workup

  1. customIt was quenched with sated aq. sodium sulfite
  2. additionThe mixture was diluted with CH2Cl2
  3. extractionaq. NaHCO3 then extracted 3× with CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cdaa6023faae4f5e811c88456ba91999
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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