Sulfuric Acid → HCID 13366430, compound

Participants

Reaction Steps

A mixture of 15.3 g (0.0375 mol) of ethyl-(2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoate, 76.5 ml of dioxane and 30 ml of 2N methanolic KOH was heated to reflux for 4 hours. The mixture was then poured into 300 ml of ice-H2O and acidified to pH 2 with 2N sulfuric acid. The yellow precipitate was extracted with 3×200 ml of chloroform, washed with sodium chloride solution and dried (MgSO4). Evaporation of the solvent gave a yellow solid, which was treated with 150 ml of hexane and filtered to give 12 g of crude (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid. Recrystallization from 200 ml of ethyl acetate gave 9.25 g of (2E,4E,6E,8E,)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid; mp 190°-193° C.

Provenance & Evidence