Potassium Hydroxide → 3,7,11,15-Tetramethylhexadeca-2,4,6,10,14-pentaenoic acid

Participants

Reaction Steps

Under argon atmosphere, potassium hydroxide (19.4 g) was dissolved in 2-propanol (200 ml) under reflux, and the solution was added dropwise with (2E, 4E, 6E, 10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid ethyl ester (48.6 g) dissolved in 2-propanol (50 ml). After the mixture was stirred for 10 minutes under reflux, ice water was added to the reaction mixture and the aqueous layer was washed with n-hexane. The aqueous layer was made acid with 10% aqueous hydrochloric acid, and then extracted with diisopropyl ether. The organic layer was washed with brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain crude (2E, 4E, 6E, 10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (35.7 g, purity: 62.2%) as orange crystals.

Provenance & Evidence