Nonan-5-ol → 5-Nonanone

HRID 1945243Notes

Reaction equation

HRID 1945243 reaction equation
IC1C=CC=CC=1S(O)(=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 27782472-iodobenzenesulfonic AcidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 104055-Nonanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

8.5 mg (0.03 mmol) of 2-iodobenzenesulfonic acid prepared by Preparation Example 1, 1.48 g (2.4 mmol) of Oxone (registered trademark) and 433 mg (3 mmol) of 5-nonanol were added to 3.75 ml ethyl acetate, and the mixture was heated at 70° C. while being stirred for ten hours. After heating, the mixture was cooled to room temperature, and the insoluble substance was removed by means of filtering. The obtained filtrate was vacuum-concentrated, and diethyl ether is added in the residue, and then an insoluble material was removed by filtering. The obtained filtrate was vacuum-concentrated, and then 5-nonanone was obtained. The yield of the obtained 5-nonanone was determined and the result is shown in Table 1.

Workup

  1. temperatureAfter heating
  2. temperaturethe mixture was cooled to room temperature
  3. customthe insoluble substance was removed by means
  4. filtrationof filtering
  5. concentrationThe obtained filtrate was vacuum-concentrated
  6. additiondiethyl ether is added in the residue
  7. customan insoluble material was removed
  8. filtrationby filtering
  9. concentrationThe obtained filtrate was vacuum-concentrated

Sources & evidence

ORD record
ord-28c73ddca10b456cb3298d9e9bc6ada1
Source dataset
uspto-grants-2013_03
Patent number
US08394995B2

Reaction notes

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