[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]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.
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