8-Methyl-non-6-ensaure → (6E)-8-Methyl-6-nonenoic acid

Participants

Reaction Steps

The obtained 8-methyl-6-nonenoic acid (isomer ratio trans:cis=29:1, 408 mg, 2.40 mmol) was again dissolved in chloroform (10 ml), and a solution of cis-2-aminocyclohexanol (249 mg, 2.16 mmol) in chloroform (5 ml) was added dropwise at room temperature. The reaction mixture was concentrated under reduced pressure, the residue was again dissolved in chloroform (3 ml), and hexane (12 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature, and the precipitated crystals were collected by filtration. Hexane (15 ml) was added to the obtained crystal, and the mixture was washed three times with 10% aqueous citric acid solution (10 ml) and once with saturated brine (10 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give trans-8-methyl-6-nonenoic acid (250 mg, 1.47 mmol, purity 98.8%, yield 35.1%).

Provenance & Evidence