Acetic Acid → 3-Acetoxycyclohexene

HRID 618984Notes

Reaction equation

HRID 618984 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=1>C(#N)C>[C:1]1(=[O:4])[CH2:2][CH2:7][CH2:6][CH:5]=[CH:10]1.[C:1]([O:4][CH:10]1[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 8079Cyclohexene

Product 2

HCID 135942-Cyclohexen-1-oneYield 41%HCID 111161483-AcetoxycyclohexeneYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction was conducted in the same manner as Example C1 except that acetic acid was employed for acetonitrile and the reaction temperature was set at 90° C. As a result, cyclohexene was transformed into 2-cyclohexen-1-one (cyclohexene-based selectivity 43%, yield 41%) and 1-acetyloxy-2-cyclohexene (cyclohexene-based selectivity 45%, yield 43%) with a transformation rate of 95%.

Workup

  1. customwas set at 90° C

Sources & evidence

ORD record
ord-e106e68b160a4fdcb9c639d8083e82e5
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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