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

HRID 1532703Notes

Reaction equation

HRID 1532703 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>CC(C)=O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:3])=[O:24]

Participants

4

Reactant 2

HCID 1087001-Nonanol, 9-bromo-HCID 131709961Jones' reagent

Product 1

HCID 5482219-Bromononanoic AcidYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2N 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.

Workup

  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

Sources & evidence

ORD record
ord-4455d165049b46fd842ba13f3da76778
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

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