Potassium Hydroxide → (2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoic acid
Reaction equation
[OH-].[K+].[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5]\[C:6]([O:8]CC)=[O:7]>CC(O)C>[CH3:3]/[C:4](/[CH:11]=[CH:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5]\[C:6]([OH:8])=[O:7]Participants
4
Procedure
Potassium hydroxide (3.0 g) was dissolved in 30 ml of 2-propanol at 100° C. The solution was added with 2-propanol solution (10 ml) of ethyl (2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate obtained in Example 3 (9.1 g, 34.5 mmol), and stirred at the same temperature for 15 minutes. The reaction mixture was added to ice-water and washed with n-hexane. The solution was neutralized with 10% hydrochloric acid and extracted with n-hexane. The resulting organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from methanol twice to obtain 1.5 g of the title compound (yield 18%) as a yellow crystal.