HCID 178476592, compound → HCID 178476593, compound

HRID 330555Notes

Reaction equation

HRID 330555 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]>S(Cl)(Cl)=O>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:8]2[CH2:7][CH2:6][C@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:10][CH2:9]2)=[O:17])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 178476592HCID 178476592, compound

Product 1

HCID 178476593HCID 178476593, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

trans-6-(4-Acetoxycyclohexyl)hexanoic acid (4.8 g) is dissolved in thionyl chloride (5 ml), and the solution is allowed to stand at room temperature for 3 days. The excess thionyl chloride is distilled off under reduced pressure togive a crude acid chloride. This product is dissolved in petroleum ether (40 ml), and ice-water (20 ml) is added. Thereafter, sodium peroxide (3 g) is added portionwise with ice-cooling and stirring. The mixture is extracted with chloroform and the extract is washed with saturated aqueous sodium chloride and dried over calcium chloride. The solvent is then distilled off under reduced pressure to give bis[trans-6-(4-acetoxycyclohexyl)hexanoyl]peroxide.

Workup

  1. distillationThe excess thionyl chloride is distilled off under reduced pressure
  2. dissolutionThis product is dissolved in petroleum ether (40 ml)
  3. additionice-water (20 ml) is added
  4. additionThereafter, sodium peroxide (3 g) is added portionwise with ice-
  5. temperaturecooling
  6. extractionThe mixture is extracted with chloroform
  7. washthe extract is washed with saturated aqueous sodium chloride
  8. dry with materialdried over calcium chloride
  9. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-82bf1b4912354e92930ba512c2fda423
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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