6,6-Dimethylhept-2-en-4-yn-1-ol → 6,6-Dimethyl-2-hepten-4-ynal
Reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[C:3]#[C:4][CH:5]=[CH:6][CH2:7][OH:8]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]([CH3:10])([CH3:9])[C:3]#[C:4][CH:5]=[CH:6][CH:7]=[O:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 6,6-dimethyl-2-hepten-4-yn-1-ol (3.56 g, 25.8S mmol) dissolved in 100 ml of freshly distilled methylene chloride was added manganese dioxide (37 g, 425 mmol) and the mixture was stirred for 17 hours. An additional 5.2 g of manganese dioxide was then added and the mixture was stirred for 2 hours, then filtered and washed copiously with methylene chloride. Evaporation of the solvent afforded 2.74 g of 6,6-dimethyl-2-hepten-4-ynal.
Workup
- stirringthe mixture was stirred for 2 hours
- filtrationfiltered
- washwashed copiously with methylene chloride
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-894e287bf6fa410994ee57e367ad91fa
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04751245
Reaction notes
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