Nonan-5-ol → 5-Nonanone

HRID 1945258Notes

Reaction equation

HRID 1945258 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]>C(OCC)(=O)C>[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 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

7.86 mg (0.03 mmol) of 2-iodo-5-methylbenzoic acid prepared by Preparation Example 3, 1.48 g (2.4 mmol) of Oxone (registered trademark) and 433 mg (3 mmol) of 5-nonanol were added to 3.75 ml of ethyl acetate, 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 to 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 the 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 to the filtrate, extraction
  6. customThe organic phase was dried

Sources & evidence

ORD record
ord-15179f767bbc4659b836ea6d59208db9
Source dataset
uspto-grants-2013_03
Patent number
US08394995B2

Reaction notes

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