Potassium Permanganate → HCID 58959948, compound

HRID 916040Notes

Reaction equation

HRID 916040 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]([CH3:26])([CH3:25])[CH2:9][C:10]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)[CH:7]=1.[Mn]([O-])(=O)(=O)=[O:30].[K+]>ClCCl.O.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]([CH3:26])([CH3:25])[CH2:9][C:10]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]([OH:30])=[O:17])=[CH:14][CH:13]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 516875Potassium Permanganate3×HCID 44435656HCID 44435656, compound

Product 1

HCID 58959948HCID 58959948, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 106 mg (0.266 mmol) 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzaldehyde in 5 mL dichloromethane was added 42 mg (0.266 mmol) of potassium permanganate and the reaction stirred at room temperature. The reaction was monitored by TLC. After several hours, a few drops of water were added and the potassium permanganate dissolved. After 1 hour, a few drops of glacial acetic acid was added followed by 42 mg (0.226 mmol) of potassium permanganate. After 4 days, the reaction was filtered through diatomaceous earth. The pH of the filtrate was adjusted (pH 6) with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The combined organics layers were washed with 1 N aqueous HCl, dried over magnesium sulfate, and concentrated to leave a light brown oil. The crude residue was concentrated from hexanes-diethyl ether to afford and off-white solid. Recrystallization from hexanes-diethyl ether gave 26 mg (24%) of the title compound, m.p. 174° C.-177° C.

Workup

  1. waitAfter several hours
  2. waitAfter 4 days
  3. filtrationthe reaction was filtered through diatomaceous earth
  4. extractionextracted with dichloromethane
  5. washThe combined organics layers were washed with 1 N aqueous HCl
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto leave a light brown oil
  9. concentrationThe crude residue was concentrated from hexanes-diethyl ether
  10. customto afford
  11. customRecrystallization from hexanes-diethyl ether

Sources & evidence

ORD record
ord-b1baf4f8ef3741dca7a0b3ad9c98f5fe
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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