Hydrochloric Acid → 10-Nonadecanone

HRID 400357Notes

Reaction equation

HRID 400357 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CON(C)[C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].Cl>C1COCC1>[CH3:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 127421-BromononaneHCID 294205HCID 294205, compoundHCID 5462224Magnesium

Product 1

HCID 1044110-NonadecanoneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Polished shaved magnesium (3.2 g, 134 mmol) was heated, and thereafter, an anhydrous THF solution (68 ml) of 1-bromononane (12.9 ml, 67.5 mmol) was slowly added dropwise thereto. After heating to reflux for 1.5 hours, the reaction solution was cooled to a room temperature, and it was then added dropwise to a THF (80 mL) solution of the N-methoxy-N-methyldecanamide (4.8 g, 22.5 mmol) obtained by the method described in Production Example D-1-1. After the obtained mixture had been stirred for 30 minutes, 1 N hydrochloric acid was added to the reaction solution, followed by extraction with diethyl ether two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane:dichloromethane=8:1), so as to obtain 10-nonadecanone (6.0 g, 95%) as a ketone body in the form of a white amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureAfter heating
  3. temperatureto reflux for 1.5 hours
  4. customobtained by the method
  5. extractionfollowed by extraction with diethyl ether two times
  6. additionAnhydrous magnesium sulfate was added to the organic layer
  7. customto dry it
  8. filtrationthe resultant was filtrated
  9. concentrationwas then concentrated
  10. customThe obtained residue was purified

Sources & evidence

ORD record
ord-af066d1ff502410bbe64e55a9b0bfefa
Source dataset
uspto-grants-2014_06
Patent number
US08741871B2

Reaction notes

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