(E)-tetradec-2-enoic acid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (E)-tetradec-2-enoic acid (18.7 g) was dissolved in anhydrous dichloromethane (200 ml) under nitrogen with stirring. The solution was cooled in ice-water bath for 30 min. Oxalyl chloride (9.1 ml) was added dropwise. The reaction mixture was slowly warm up to room temperature overnight. The solvent was removed under vacuum. The product was obtained as clear oil (20.0 g, 99%) and used in next step synthesis without further purification. The solvent was removed under vacuum

反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a dry flask containing malonic acid (56.5 g) and pyridine (132 ml) was added dodecanal (100 g) dropwise to maintain the internal temperature under 35° C. under nitrogen atmosphere while stirring. After the addition, piperidine (4 ml) was added. The reaction mixture was then heated to 55° C. for 1 hr and 90° C. for 3 hrs. The mixture was cooled to room temperature and poured into ice-water (˜1 L). After the addition of 400 ml 6M HCl, the mixture was extracted with ethyl acetate (2 L). The ethyl acetate phase was washed with DI water twice. The solvent was removed under vacuum. The crude product was crystallized from hexane. The pure product was obtained as a white solid (80.5 g, 65.6% yield). Proton NMR(CDCl3) δ 0.88 (t, 3H), 1.26 (m, 16H), 1.45 (m, 2H), 2.22 (m, 2H), 5.82 (td, 1H), 7.09 (td, 1H). was added The reaction mixture was then heated to 55° C. for 1 hr and 90° C. for 3 hrs The mixture was cooled to room temperature the mixture was extracted with ethyl acetate (2 L) The ethyl acetate phase was washed with DI water twice The solvent was removed under vacuum The crude product was crystallized from hexane