Water → Ketoisophorone

HRID 2372913Notes

Reaction equation

HRID 2372913 reaction equation
C1(C)C=CC=CC=1.[O:8]=[C:9]1[CH2:16][C:13]([CH3:15])([CH3:14])[CH2:12][C:11]([CH3:17])=[CH:10]1.[OH2:18]>[O-]S([O-])(=O)=O.[Cu+2].CCCCCC>[CH3:17][C:11]1[C:12](=[O:18])[C:13]([CH3:15])([CH3:14])[CH2:16][C:9](=[O:8])[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 6544Isophorone

Product 1

HCID 62374Ketoisophorone

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 8058HexaneSolvent2×

Procedure

A 1-1 three-neck flask equipped with a gas inlet frit, a stirrer and an intensive condenser was charged with 350 ml of toluene, 350 g of isophorone, 11.4 g of H3 [P(Mo3O10)4 ]×H2O, 1.4 g of CuSO4 ·5H2O and 1.4 g of MoO3. After compressed air had been passed through at 110° C. for 90 hours, the reaction mixture was added a little at a time at 80° C. into 4 1 of boiling n-hexane. The mixture was then filtered, and the filtrate was concentrated in a rotary evaporator. The yellowish oil obtained by distillation at 97° C./13 mbar was converted into almost colorless crystals at -18° C. by addition of 10% by volume of n-hexane.

Workup

  1. customA 1-1 three-neck flask equipped with a gas inlet frit, a stirrer and an intensive condenser
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated in a rotary evaporator
  4. customThe yellowish oil obtained by distillation at 97° C./13 mbar

Sources & evidence

ORD record
ord-3a3c1ed0243d41f297a97f0fa0951655
Source dataset
uspto-grants-1992_03
Patent number
US05101032

Reaction notes

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