Acetic Acid → 3-Acetoxycyclohexene

HRID 742814Notes

Reaction equation

HRID 742814 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.OO.[C:9]([OH:12])(=[O:11])[CH3:10]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]([O:12][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 8079Cyclohexene

Product 1

HCID 111161483-AcetoxycyclohexeneYield 50%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A 500 ml three-neck flask was charged with 15 g of cyclohexene (0.18 moles), 150 g of acetic acid and 80 mg of palladium acetate (0.36 mmoles). The temperature was taken to 50°, and then 10.6 g (0.22 moles) of 70% by weight hydrogen peroxide were introduced in 8 h. The reaction was continued for 2 more hours, while keeping the temperature at 50°. The acetic acid was then distilled (35°, 20×102Pa). The residue was distilled under vacuum (64°-68°, 15×102Pa) to provide cyclohex-2-en-1-yl acetate, 90% pure (13 g, yield 50%). cyclohex-2-en-1-yl-acetate

Workup

  1. customwas taken to 50°
  2. customat 50°
  3. distillationThe acetic acid was then distilled (35°, 20×102Pa)
  4. distillationThe residue was distilled under vacuum (64°-68°, 15×102Pa)

Sources & evidence

ORD record
ord-71a1b52b81d44cfc915494adac8c282e
Source dataset
uspto-grants-1996_09
Patent number
US05554786

Reaction notes

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