Hydrochloric Acid → 9-Fluorononanoic acid

A solution of methyl 9-fluorononanoate (17.1 g, 90 mmol) in 1,4-dioxane (45 mL) was treated drop-wise with a solution of lithium hydroxide (2.4 g, 100 mmol) in water (15 mL). The reaction mixture was stirred at ambient temperature until no starting material remained by thin layer chromatography. The reaction mixture was acidified to pH 1.0 with 2N hydrochloric acid and extracted with diethyl ether. The combined organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, through a short pad of silica gel, and the filtrate evaporated in vacuo to yield 9-fluorononanoic acid (12.75 g, 72 mmol) as a clear, colorless oil, which solidified on standing in the refrigerator. The product was used without further purification.

1. extractionextracted with diethyl ether
2. washThe combined organic phase was washed with water
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered, through a short pad of silica gel
5. customthe filtrate evaporated in vacuo

ORD record

ord-dc3e0b204a664697ab1f0c930794a69b

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06605618B2