Ozone → (2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate

HRID 1607352Notes

Reaction equation

HRID 1607352 reaction equation
[O:1]=[O+][O-].[CH3:4][C:5]1([CH3:29])[CH:7]([CH:8]=C(C)C)[CH:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]=1[CH3:28])=[O:13]>C(OCC)(=O)C>[CH3:4][C:5]1([CH3:29])[CH:7]([CH:8]=[O:1])[CH:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]=1[CH3:28])=[O:13]

Participants

4

Reactant 2

HCID 24823OzoneHCID 13933694(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

Product 1

HCID 13602235(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ozone was bubbled at -78° C. into a solution of 698 mg (2.01 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate obtained in Reference Example 1, in 10 ml of ethyl acetate. The supply of ozone was terminated when the solution turned slightly blue. Then, 1 ml of dimethyl sulfide was added, and the temperature of the mixture was allowed to warm to room temperature. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (dichloromethane/hexane=1/1) to obtain 591 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate.

Workup

  1. customThe supply of ozone was terminated when the solution
  2. additionThen, 1 ml of dimethyl sulfide was added
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (dichloromethane/hexane=1/1)

Sources & evidence

ORD record
ord-c426992e5f4a4f47a205ae05405fd724
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

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