Water → HCID 86672617, compound

HRID 2369268Notes

Reaction equation

HRID 2369268 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:31])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:9][CH2:10][CH2:11][C:12](OC)=[O:13].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:31])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:30])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 54269534HCID 54269534, compound

Product 1

HCID 86672617HCID 86672617, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, 9.6 g (0.25 mol) of lithium aluminum hydride was added little by little at 0° C. to a solution of 150 g (0.425 mol) of methyl 5,9,13,17-tetramethyloctadec-4-enoate in dry tetrahydrofuran (850 mL). After being stirred at 50° C. for 2 hours, the reaction mixture was cooled on ice, followed by careful addition of water until the resulting gray suspension turned white. Sodium sulfate was added to the solution at room temperature for drying. After filtration, the filtrate was concentrated to obtain 133.8 g of the title compound (97% yield) as a colorless transparent liquid. The results of NMR analysis of the resulting compound are as shown below.

Workup

  1. temperaturethe reaction mixture was cooled on ice
  2. customfor drying
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fff2e97bbeda4c8193ed9bc21d8805f9
Source dataset
uspto-grants-2014_04
Patent number
US08703922B2

Reaction notes

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