Peracetic Acid → HCID 54081276, compound

HRID 1076486Notes

Reaction equation

HRID 1076486 reaction equation
[CH3:1][C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:22])[CH2:20][CH3:21])=[CH:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][O:13]2)=[CH:8][CH:7]=1.C([O-])(=[O:25])C.[Na+].C(OO)(=O)C>C(Cl)(Cl)Cl>[O:25]1[C:19]([CH3:22])([CH2:20][CH3:21])[CH:18]1[CH2:17][CH2:16][C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][O:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 54421045HCID 54421045, compound

Product 1

HCID 54081276HCID 54081276, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 118.8 g. of 7-(3,7-dimethyl-2,6-nonadienyloxy)-chromane, 26 g. of anhydrous sodium acetate in 910 ml. of chloroform is treated over a period of 1 hour with 80 g. of 40% peracetic acid while stirring and flushing with nitrogen at 0°-2°C. The resulting mixture is subsequently stirred for an additional 15 minutes. The mixture is washed successively with a saturated sodium chloride solution, 10% sodium bicarbonate 0.1-N sodium thiosulphate solution and water, dried over sodium sulphate and concentrated. By filtration over 600 g. of silica gel with hexane/ether (9:1) and subsequent molecular distillation, there is obtained 7-(6,7-epoxy-3,7-dimethyl-2-nonenyloxy)-chromane, nD20 = 1.5295.

Workup

  1. additionA mixture of 118.8 g
  2. customflushing with nitrogen at 0°-2°C
  3. washThe mixture is washed successively with a saturated sodium chloride solution, 10% sodium bicarbonate 0.1-N sodium thiosulphate solution and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. filtrationBy filtration over 600 g
  7. distillationof silica gel with hexane/ether (9:1) and subsequent molecular distillation

Sources & evidence

ORD record
ord-910cb1fa78b64402bb5e1b1df4f5013b
Source dataset
uspto-grants-1976_05
Patent number
US03957763

Reaction notes

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