Methanol → beta Farnesene

Participants

Reaction Conditions

Reaction Steps

In a 75 mL Keim autoclave, containing a stirring bar, were placed (E)-7,11-dimethyl-3-methylenedodeca-1,6,10-triene (1.00 g, 4.89 mmol) in THF (20 ml). Methanol (200 μl, 4.94 mmol) and PdCl2(PPh3)2 (80 mg, 0.114 mmol) were added. Then the reactor was sealed and the mixture purged with 3×10 bar of carbon monoxide (CO). While stiffing, the autoclave was pressurized to 40 bar with CO and then heated in an oil bath at 90° C. Once the temperature equilibrated to the set point, the autoclave was pressurized to 67 bar with CO and the reaction allowed to proceed under these conditions for 64 h. Then the reaction mixture was concentrated on a rotary evaporator to give a crude residue which was subsequently distilled on a Kugelrohr apparatus (0.3 mbar/170° C.) to afford a colorless liquid (1.17 g) containing (3E,7E)-homofarnesic acid methyl ester and (3Z,7E)-homofarnesic acid methyl ester (61%, 2/1).

Provenance & Evidence