Sodium Hydroxide → HCID 86624385, compound

HRID 909688Notes

Reaction equation

HRID 909688 reaction equation
C([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([NH-:36])=O)CCCCCCCCCCCCCCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[OH-].[Na+]>C1COCC1.CCOCC>[CH2:32]([NH:36][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]/[CH:26]=[CH:25]\[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 178442860HCID 178442860, compound

Product 1

HCID 86624385HCID 86624385, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

20 ml 1M LiAlH4 in ether are provided under argon inert gas in a 250 ml three-neck flask having a dropping funnel and a reflux condenser and subsequently a solution of 7.59 g (15 mmol) palmityloleoylamide in 80 ml THF added dropwise within 20 minutes. The mixture is refluxed for 2.5 hours, then another 5 ml 1 M LiAlH4 in ether is added and refluxed for another 2.5 hours. Excess hydride is decomposed using 6 M NaOH under ice bath cooling and the precipitate is filtered off. The precipitate is extracted twice with 40 ml of hot MtBE each, the combined organic phases dried over Na2SO4 and the solvent removed using a rotary evaporator. The residue is crystallised from 100 ml MtBE at −20° C. 6.23 g (12.7 mmol) corresponding to a yield of 85% of a colourless crystalline solid are obtained.

Workup

  1. temperatureThe mixture is refluxed for 2.5 hours
  2. temperaturerefluxed for another 2.5 hours
  3. temperaturecooling
  4. filtrationthe precipitate is filtered off
  5. extractionThe precipitate is extracted twice with 40 ml of hot MtBE each, the combined organic phases
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed
  8. customa rotary evaporator
  9. customThe residue is crystallised from 100 ml MtBE at −20° C

Sources & evidence

ORD record
ord-7e6a92eb695941908a1f4e4db9937e7c
Source dataset
uspto-grants-2011_09
Patent number
US08017804B2

Reaction notes

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