Methane → HCID 13595902, compound

HRID 742818Notes

Reaction equation

HRID 742818 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]=[CH2:6].[C:7]1(=[O:14])[CH:12]=CC(=O)C=C1.C.[OH:16]O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[C:7]([O:14][CH:2]1[CH2:3][CH2:4][C:5](=[CH2:6])[CH2:1]1)(=[O:16])[CH3:12]

Participants

7

Reactant 4

HCID 297MethaneHCID 784Hydrogen PeroxideHCID 4650QuinoneHCID 115981,5-Hexadiene

Product 1

HCID 13595902HCID 13595902, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

Acetoxylation of l'hexa-1,5-diene ##STR3## A 500 ml three-neck flask is charged with 15 g of hexa-1,5-diene (0.18 moles), 150 g of acetic acid, 0.77 g of benzoquinone (7 mmoles), 1 g of charcoal and 80 mg of palladium acetate (0.35 mmoles). The temperature is taken to 50°, then 7 g (0.14 moles) of 70% by weight hydrogen peroxide are introduced in 8 h, and the reaction is allowed to proceed for a further 2 h while maintaining the temperature at 50°. The acetic acid is then distilled (35°, 20×102Pa). The residue is distilled under vacuum to provide 1-acetoxy-3-methylene-cyclopentane in 65% molar yield. 1-acetoxy-3-methylene-cyclopentane

Workup

  1. customis taken to 50°
  2. temperaturewhile maintaining the temperature at 50°
  3. distillationThe acetic acid is then distilled (35°, 20×102Pa)
  4. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-56a76983bb564c8da0a9820665779f30
Source dataset
uspto-grants-1996_09
Patent number
US05554786

Reaction notes

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