Acetic Acid → 2-Methyl-cyclohex-2-en-1-yl acetate

HRID 742817Notes

Reaction equation

HRID 742817 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1.C.OO.[C:11]([OH:14])(=[O:13])[CH3:12]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(=O)C=CC(=O)C=C1>[C:11]([O:14][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]=[C:2]1[CH3:1])(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 784Hydrogen PeroxideHCID 115741-Methylcyclohexene2×

Product 1

HCID 126351582-Methyl-cyclohex-2-en-1-yl acetateYield 50%

Reagents, catalysts & solvents 2

HCID 4650QuinoneCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Acetoxylation of 1-methylcyclohexene A 500 ml three-neck flask is charged with 15 g of 1-methylcyclohexene (0.15 moles), 150 g of acetic acid, 0.77 g of benzoquinone (7 mmoles), 1 g of active charcoal and 80 mg of palladium acetate (0.35 mmoles). The temperature is taken to 50°, then 8 g (0.17 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 (75°-80°, 15×102Pa) to provide 2-methyl-cyclohex-2-en-1-yl acetate (11 g, yield 50%).

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 (75°-80°, 15×102Pa)

Sources & evidence

ORD record
ord-76276fc7061f418eada8083114d19b48
Source dataset
uspto-grants-1996_09
Patent number
US05554786

Reaction notes

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