Water → 3,3-Dimethyl-5-oxohexanoic acid

HRID 1981072Notes

Reaction equation

HRID 1981072 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4](C)=[CH:3]1.O=O.[O:13]=[O+][O-].[OH2:16]>ClCCl>[CH3:7][C:6]([CH3:8])([CH2:9][C:2](=[O:1])[CH3:3])[CH2:5][C:4]([OH:13])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 977OxygenHCID 6544IsophoroneHCID 24823Ozone2×

Product 1

HCID 113326103,3-Dimethyl-5-oxohexanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16 g of isophorone in 100 g of dichloromethane was cooled down to 0° C. A stream of oxygen, which contained about 4 percent of ozone, was conducted through this solution until the solution was saturated with ozone. Then the ozonolyzed solution was added drop by drop into 150 ml of boiling water, the dichloromethane was distilled off and the aqueous solution was boiled for another 3 hours. The 3,3-dimethyl-5-oxo-hexanoic acid formed was isolated by reducing under vacuum.

Workup

  1. distillationthe dichloromethane was distilled off

Sources & evidence

ORD record
ord-b9c8484c1e084e0abc64c8013adfdef4
Source dataset
uspto-grants-1985_04
Patent number
US04511734

Reaction notes

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