Sodium Thiosulfate → HCID 12790262, compound

HRID 848426Notes

Reaction equation

HRID 848426 reaction equation
[CH3:1][C:2]12[CH2:8][CH:7]([OH:9])[CH:6]1[C:5]([CH3:11])([CH3:10])[C:4](=[O:12])[CH2:3]2.ClC1C=CC=C(C(OO)=[O:21])C=1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:1][C:2]12[CH2:8][CH:7]([OH:9])[CH:6]1[C:5]([CH3:10])([CH3:11])[O:21][C:4](=[O:12])[CH2:3]2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 12790261HCID 12790261, compound

Product 1

HCID 12790262HCID 12790262, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 400 mg of the hydroxyketone (IV) in 8 ml of methylene chloride, while being cooled in ice, were added 770 mg of m-chloroperbenzoic acid and 480 mg of sodium hydrogencarbonate. The mixture was stirred overnight at room temperature and then treated with 10 ml of 10% sodium thiosulfate solution. The aqueous layer was separated and extracted three time with methylene chloride. The combined methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution, then with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 415 mg of a colorless oil (III); nD20 1.4845; MS: m/e 169 (M+ --CH3), 166 (M+ --H2O).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted three time with methylene chloride
  3. washThe combined methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialwith an aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7be15e461ed84d0c87a29e41c9bbc3d7
Source dataset
uspto-grants-1981_10
Patent number
US04296036

Reaction notes

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