Ozone → 2-Difluoromethyloxy-4,6-dimethylphenylacetaldehyde
Reaction equation
[F:1][CH:2]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[CH2:13][CH:14]=C)[F:3].[O:16]=[O+][O-]>ClCCl>[F:1][CH:2]([F:3])[O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[CH2:13][CH:14]=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
16.5 g of 3,5-dimethyl-2-(2-propen-1-yl)-phenyl difluoromethyl ether were dissolved in 50 ml of dichloromethane and the solution was cooled to −70° C. Ozone was passed through the solution for one hour until the olefin was no longer detectable. The vessel was subsequently flushed with a stream of nitrogen, 13.7 g of dimethyl sulphide were added, and stirring of the mixture was continued for 30 minutes. The solution was warmed to room temperature and stirring was continued for a further 30 minutes. After the solution was free from peroxides, it was concentrated, and the residue was employed in the next reaction without further purification. 19.2 g of 2-difluoromethyloxy-4,6-dimethylphenylacetaidehyde were obtained as crude product.
Workup
- customThe vessel was subsequently flushed with a stream of nitrogen, 13.7 g of dimethyl sulphide
- additionwere added
- temperatureThe solution was warmed to room temperature
- stirringstirring
- waitwas continued for a further 30 minutes
- concentrationwas concentrated
- customthe residue was employed in the next reaction without further purification
Sources & evidence
- ORD record
- ord-5a2cf1c717c84e48982dc076b58a8497
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06358887B1
Reaction notes
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