Cyclohexanone → Cyclohexene-1-yl acetate

HRID 1076087

Reaction equation

HRID 1076087 reaction equation
C1(=O)CCCCC1.[H][H].[C:10]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:12])[CH3:11]>C(O)(=O)C>[C:10]([O:13][C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 12146Cyclohexyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 74019Cyclohexene-1-yl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid in an amount of 15.1 g. was reacted with 6.1 g. cyclohexanone over the catalyst (0.5 g.) described in Example 1. The reaction started at room temperature (25°C.) in the presence of hydrogen and was stopped after 95 minutes, the temperature reaching a high of 84°C. by application of heat. Cyclohexyl acetate was identified as a reaction product by VPC analysis. This reaction in the presence of Amberlyst-15 resin gives a small amount of 1-acetoxycyclohexene; with conventional platinum-on-alumina catalyst it gives cyclohexanol; and with a loose physical mixture of Amberlyst-15 resin and the conventional platinum-on-alumina, the product is cyclohexanol. By "loose" physical mixture is meant a slurry of the type described in Example 2.

Workup

  1. customwas reacted with 6.1 g
  2. customstarted at room temperature
  3. custom(25°C.)
  4. customhigh of 84°C.
  5. temperatureof heat
  6. customThis reaction in the presence of Amberlyst-15 resin

Sources & evidence

ORD record
ord-b64d2b1d2ae242f08de1f8ccc44a119f
Source dataset
uspto-grants-1976_05
Patent number
US03954883

Linked notes

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