1,5-Dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene → 5-Hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienal

Participants

Reaction Steps

1.22 g (4 mmol) of 1,5-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene (I) was dissolved in 30 ml of methylene chloride, to which was then added 3.48 g (40 mmol) of manganese dioxide and the mixture was stirred at an ambient temperature for 24 hours. After the resulting mixture was diluted with ether, it is dried over anhydrous magnesium sulfate and filtered, followed by evaporation of ether to obtain 5-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienal (II) as a mixture of E and Z isomers in a yield of 90%.

Provenance & Evidence