Methanol → beta Farnesene

Temperature

90 °C

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).

1. additionIn a 75 mL Keim autoclave, containing a stirring bar
2. customThen the reactor was sealed
3. customthe mixture purged with 3×10 bar of carbon monoxide (CO)
4. concentrationThen the reaction mixture was concentrated on a rotary evaporator
5. customto give a crude residue which
6. distillationwas subsequently distilled on a Kugelrohr apparatus (0.3 mbar/170° C.)

ORD record

ord-b00f1189fcaf4014ab5e714772185a3c

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376365B2