Sodium Sulfite → HCID 59442695, compound

HRID 657498Notes

Reaction equation

HRID 657498 reaction equation
[CH3:1][O:2][C:3]1([C:18]2[CH:23]=[CH:22][C:21](SC)=[CH:20][CH:19]=2)[CH2:8][CH2:7][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl[C:27]1C=CC=C(C(OO)=O)C=1.[S:37]([O-:40])([O-])=[O:38].[Na+].[Na+].S([O-])(O)(=O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1([C:18]2[CH:19]=[CH:20][C:21]([S:37]([CH3:27])(=[O:40])=[O:38])=[CH:22][CH:23]=2)[CH2:8][CH2:7][C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516919Sodium BisulfateHCID 59442506HCID 59442506, compound

Product 1

HCID 59442695HCID 59442695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

690 mg of 4-methoxy-4-(4-methylsulfanylphenyl)-1-phenylcyclohexanecarboxylic acid were dissolved in 30 ml of DCM and 865 mg of 3-chloroperbenzoic acid were added at room temperature. The reaction mixture was stirred at room temperature was for 5 h and 40 min. 60 ml of a saturated aqueous sodium sulfite solution were then added, the mixture was stirred for 15 min at room temperature, adjusted to pH=3 with a saturated aqueous sodium hydrogensulfate solution and extracted three times with 100 ml each of DCM. The combined extracts were dried over magnesium sulfate and the solvent was removed in vacuo. Chromatography of the residue on silica gel with MTB yielded 464 mg of the title compound as an amorphous solid.

Workup

  1. stirringthe mixture was stirred for 15 min at room temperature
  2. extractionextracted three times with 100 ml each of DCM
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-121e5450fffe47c1b4bface9f904e59a
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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