Hydrochloric Acid → (2E)-2-Tetradecenoic acid

Temperature

35 °C

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).

1. additionwas added
2. temperatureThe reaction mixture was then heated to 55° C. for 1 hr and 90° C. for 3 hrs
3. temperatureThe mixture was cooled to room temperature
4. extractionthe mixture was extracted with ethyl acetate (2 L)
5. washThe ethyl acetate phase was washed with DI water twice
6. customThe solvent was removed under vacuum
7. customThe crude product was crystallized from hexane

ORD record

ord-c5ea31e78fad4b239185f78da9b8a87a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403760B2