Hydrochloric Acid → (2E)-hepta-2,6-dienoic acid

Temperature

90 °C

4-Pentenal (4.45 g, 51.4 mmol) and malonic acid (6.41 g, 61.6 mmol) were dissolved in pyridine (9.9 mL). To the solution, piperidine (1.9 mL) was added, and the mixture was then stirred at 90° C. for 5 hours. The mixture was allowed to cool and then made acidic by the addition of 2 N hydrochloric acid, followed by extraction with diethyl ether. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the filtrate was then concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain the compound of interest as a colorless oil substance (3 mmHg, 110-116° C., 3.27 g, 50%).

1. temperatureto cool
2. extractionfollowed by extraction with diethyl ether
3. washThe organic layer was washed with saturated saline
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationthe filtrate was then concentrated under reduced pressure
6. distillationThe residue was distilled under reduced pressure
7. customto obtain the compound of interest as a colorless oil substance (3 mmHg, 110-116° C., 3.27 g, 50%)

ORD record

ord-d3bf4d49245c45bcabf983cbe3463d62

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324425B2