3-Isopropenyl-1-methyl-2-methylenecyclopentan-1-ol → 2-(2-Formyl-3-methyl-2-butenyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

Participants

Reaction Conditions

Reaction Steps

A mixture of 7.6 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol and 8.1 g of 1,1-dimethoxy-3-methyl-3-butene was heated under nitrogen in an oil bath of 100°C for 15 hours in the presence of 100 mg of freshly prepared dry pyridine hydrochloride with continuous removal of the methanol formed. The mixture was then heated for 7 hours to 150°C and finally poured on to a mixture of ice and ether. The ethereal phase was washed with bicarbonate solution and water, dried with anhydrous magnesium sulphate and concentrated under reduced pressure. After distillation of the oily crude product, there were obtained 6.5 g of 2-(2-formyl-3-methyl-2-butenyl)-3-isopropenyl-1-methyl-cyclopent-1-ene; boiling point 0.003 about 80°C; nD20 = 1.5148; IRfilm : μmax = 3100, 2780, 1675, 1635, 1440, 1375, 1155, 1060 and 895 cm-1. The compound has a woody, floral, fruitily sweetish fragrance.

Provenance & Evidence