Malonic Acid → HCID 86644217, compound

At room temp., a piperidinium acetate solution, freshly prepared by mixing piperidine (35.0 μL, 0.354 mmol) and acetic acid (19.0 μL, 0.332 mmol) in dimethyl sulfoxide (1.00 mL), was injected into a stirred solution of the prepared hept-5-ynal (1.50 g, 13.6 mmol) and malonic acid (2.83 g, 27.2 mmol) in dimethyl sulfoxide (50 mL). After refluxing the reaction mixture for 4 h, water (10 mL) and ether (20 mL) were added at room temp., and the layers were separated. The aqueous layer was extracted with ether (3×25 mL), and the combined organic extracts were washed with water (25 mL), dried (Na2SO4), and concentrated under reduced pressure. Kugelrohr distillation at 149° C./14 mbar furnished (3E)-non-3-en-7-ynoic acid (902 mg, 44%) as colorless crystals (mp 43-45° C.).

1. temperatureAfter refluxing the reaction mixture for 4 h
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with ether (3×25 mL)
4. washthe combined organic extracts were washed with water (25 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. distillationKugelrohr distillation at 149° C./14 mbar

ORD record

ord-20e5c06706c24d5aaf37e7af1ab364dc

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217185B2