40137-00-6 → HCID 11042011, compound

Participants

Reaction Steps

A mixture of 2.27 g (10.0 mmol) of (Z)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine, 36 mg (0.041 mmol) of [θ4 -(Z,Z)-1,5-cyclooctadiene][(R)-6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine)]rhodium(I) tetrafluoroborate and 5 ml of tetrahydrofuran was heated to 85°-90° C. for 16 hours in a sealed tube. The brownish reaction mixture was evaporated and the residue was distilled in a bulb-tube at about 150° C./0.2 mbar, whereby 2.1 g of (1E, 3R)-N,N-diethyl-3,7-dimethyl-1,6-octadienylamine were obtained as a colourless oil. The distillate obtained was diluted with hexane, treated with 5 ml of 50% acetic acid and the mixture was stirred for 1 hour. The phases were separated and the organic phase was washed with water. 1N HCl, saturated NaHCO3 solution and saturated NaCl solution, dried over Na2SO4, filtered and evaporated. After distillation in a bulb-tube at about 130° C./15 mbar there were obtained 1.38 g (90%) of (R)-citronellal [(R)-3,7-dimethyl-6-octenal] as a colourless liquid.

Provenance & Evidence