Hydrochloric Acid → HCID 21242373, compound

Participants

Reaction Steps

A solution of 4.8 g of (E,E)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienamide in 70 ml of toluene is treated with 4.48 g of aluminum isopropylate, whereupon the mixture is boiled under reflux for 4.5 hours. The cooled reaction mixture is poured into a mixture of 2N hydrochloric acid and ice, whereupon the mixture is extracted with 2×100 ml of ether. The combined organic extracts are washed with water and with saturated sodium bicarbonate solution, dried over sodium sulphate, filtered and evaporated. The residue is chromatographed on 230 g of aluminum oxide (basic, activity III), elution being carried out with hexane-ethyl acetate (20% to 100%) and then with ethyl acetate-methanol (10%). There is obtained (E,E)-10-hydroxy-3,7,11-trimethyl-2,6,11-dodecatrienamide as a yellowish, viscous oil. IR (film): 3335, 3195 (OH and NH2); 1668 (amide C=O). MS (CI with NH3): 252 (M+H)+ ; 251 (M+NH4 -H2O)+.

Provenance & Evidence