1-Nonanol, 9-bromo- → 9-Bromononanoic Acid

2 N Jones' reagent (20 ml) was gradually and dropwise added to an acetone (20 ml) solution of 9-bromononanol (2.2 g,10 mmols) with cooling with ice, and then stirred at room temperature for 10 minutes. The reaction mixture was extracted three times with hexane (40 ml). The organic layer was washed with water, and then extracted three times with an aqueous saturated solution of potassium carbonate (40 ml). The aqueous layers were combined, then made acidic (pH=1) with 10% sulfuric acid added thereto, and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. 1.8 g (yield: 77%) of 9-bromononanoic acid was obtained as colorless needle-like crystals.

1. temperaturewith cooling with ice
2. extractionThe reaction mixture was extracted three times with hexane (40 ml)
3. washThe organic layer was washed with water
4. extractionextracted three times with an aqueous saturated solution of potassium carbonate (40 ml)
5. additionadded
6. extractionextracted with ethyl acetate
7. washThe resulting organic layer was washed with water and saturated saline in that order
8. dry with materialdried with anhydrous sodium sulfate
9. customthe solvent was evaporated

ORD record

ord-65cc00d5c6bd46f3aa80c7a35716e29d

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825223B2