Hydrogen Peroxide → HCID 21436328, compound

HRID 2397613Notes

Reaction equation

HRID 2397613 reaction equation
[OH:1]O.[OH:3][CH:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH2:10][S:9](=[O:13])[CH:8]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C(Cl)(Cl)Cl>CO.O>[OH:3][CH:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH2:10][S:9](=[O:1])(=[O:13])[CH:8]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 6212ChloroformHCID 21436340HCID 21436340, compound

Product 1

HCID 21436328HCID 21436328, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

30% Hydrogen peroxide (2.0 ml., 20 millimole) is added slowly to a stirred solution of 7-[3-(3-hydroxyoctyl)-1,4-dioxo-2-thiazolidinyl]heptanoic acid (1.98 g., 4.69 millimole) and ammonium molybdate. tetrahydrate 0.1 g., catalyst) in methanol (25 ml.) maintained at 0° to 5° C. The resulting solution is allowed to warm to room temperature and then is stirred at room temperature for 64 hours. After diluting with water, the reaction mixture is extracted with chloroform three times. The combined organic extract is washed with water until free of peroxides, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo at 40° to 50° C. leaves a viscous oil which is applied to a silica gel (20 g.) column with chloroform. Elution with chloroform-acetic acid (25:1; v:v) provides the title compound as a tlc homogeneous oil.

Workup

  1. extractionthe reaction mixture is extracted with chloroform three times
  2. extractionThe combined organic extract
  3. washis washed with water until free of peroxides
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customEvaporation of the filtrate in vacuo at 40° to 50° C.
  7. customleaves a viscous oil which
  8. washElution with chloroform-acetic acid (25:1; v:v)

Sources & evidence

ORD record
ord-bf3521d09cb14231a22dffd9e6b7d029
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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