Nonan-5-ol → 5-Nonanone

HRID 1945259Notes

Reaction equation

HRID 1945259 reaction equation
IC1C=CC(C)=CC=1C(O)=O.OOS([O-])=O.[K+].[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]([OH:27])[CH2:23][CH2:24][CH2:25][CH3:26]>[N+](C)([O-])=O>[CH3:18][CH2:19][CH2:20][CH2:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 12202Nonan-5-olHCID 1429412-Iodo-5-methylbenzoic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 104055-Nonanone

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
70 °C

Procedure

1.57 mg (0.006 mmol) of 2-iodo-5-methylbenzoic acid prepared by Preparation Example 3, 1.11 g (1.8 mmol) of powdered Oxone (registered trademark) and 433 mg (3 mmol) of 5-nonanol were added to 3.75 ml of nitromethane, and the mixture was heated at 70° C. while being stirred for 12 hours. After being heated, the mixture was cooled to room temperature, and the insoluble substance was removed by means of filtering. Water was added in the filtrate, extraction was carried out using diethyl ether. The organic phase was dried by using sodium sulfate, and then 5-nonanone was obtained by means of vacuum-concentration. The yield of the obtained 5-nonanone was determined and the result is shown in Table 1.

Workup

  1. temperatureAfter being heated
  2. temperaturethe mixture was cooled to room temperature
  3. customthe insoluble substance was removed by means
  4. filtrationof filtering
  5. additionWater was added in the filtrate, extraction
  6. customThe organic phase was dried

Sources & evidence

ORD record
ord-28d804917361414e816455430fceb2de
Source dataset
uspto-grants-2013_03
Patent number
US08394995B2

Reaction notes

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