Hydrogen Peroxide → HCID 13215910, compound

HRID 1027965Notes

Reaction equation

HRID 1027965 reaction equation
C1=CCCC=CCC1.[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1.[CH2:15]([O:17][C:18](=[O:22])[CH:19](Cl)[Cl:20])[CH3:16].CC([O-])(C)C.[K+].C([O-])(=O)C.[Na+].OO.[Na+].[Cl-]>C(O)(C)(C)C.C1COCC1>[Cl:20][CH:19]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:18]([O:17][CH2:15][CH3:16])=[O:22]

Participants

10

Reactant 7

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 8079CyclohexeneHCID 10808Ethyl dichloroacetateHCID 517045Sodium AcetateHCID 10937607HCID 10937607, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13215910HCID 13215910, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

100 mL of 1M BH3-THF complex (100 mmol) were added to 170 mL of dry THF under a blanket of nitrogen at room temperature. 12.3 mL of cis-1,5-cyclooctadiene (100 mmol) were added dropwise to this mixture within a period of 5 minutes, and the temperature rose to 45° C. The reaction mixture was heated under reflux over a period of 1.5 h, again cooled to 45° C., and 10.1 mL of cyclohexene (100 mmol) were added and stirring was continued for a further 2 h at 45° C. After the reaction mixture had been cooled in an ice bath, 12.2 mL of ethyldichloroacetate (100 mmol) in 50 mL of tert-butanol were added, stirring was continued for a further 15 minutes and 1M potassium tert-butylate (100 mmol, 100 mL) was added dropwise within a further 15 minutes. The reaction mixture was then stirred over a period of 15 minutes, 33 mL of 3M sodium acetate solution (100 mmol) were added and 22.5 mL of 30% strength aq. H2O2 solution (750 mmol) were added dropwise. The mixture was stirred at room temperature over a period of 30 minutes, then salted out with NaCl, the organic phase dried over MgSO4 and the solvent removed under reduced pressure. Following washing of the residual solid matter with tert-butylmethyl ether, cyclohexane/tert-butylmethyl ether (9:1), tert-butylmethyl ether, and EA, there were obtained 7.6 g (37.4%) of product.

Workup

  1. customrose to 45° C
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux over a period of 1.5 h
  4. temperatureAfter the reaction mixture had been cooled in an ice bath
  5. stirringstirring
  6. waitwas continued for a further 15 minutes
  7. stirringThe reaction mixture was then stirred over a period of 15 minutes
  8. stirringThe mixture was stirred at room temperature over a period of 30 minutes
  9. dry with materialthe organic phase dried over MgSO4
  10. customthe solvent removed under reduced pressure
  11. washFollowing washing of the residual solid matter with tert-butylmethyl ether, cyclohexane/tert-butylmethyl ether (9:1), tert-butylmethyl ether, and EA

Sources & evidence

ORD record
ord-8b7343b1ec484a4db8fda380c9b341ef
Source dataset
uspto-grants-2014_05
Patent number
US08735426B2

Reaction notes

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