Aluminium lithium hydride → 2,2-Ditetradecylpropane-1,3-diol

HRID 1858877Notes

Reaction equation

HRID 1858877 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:12](OCC)=[O:13])C>C1COCC1>[CH2:31]([C:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:10][OH:9])[CH2:12][OH:13])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22121587HCID 22121587, compound

Product 1

HCID 221215792,2-Ditetradecylpropane-1,3-diolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (9.68 mmol) is added to a diethyl-2,2-ditetradecylmalonate (2.42 mmol) solution in THF at rt and the reaction mixture is heated under reflux for 2 h. The reaction mixture is quenched with 1 M HCl solution and stirred for 30 min. The aqueous layer is extracted with diethyl ether two times. The combined organic layers are washed with a dilute HCl solution and brine, and then dried over anhydrous magnesium sulfate. Solvents are evaporated under vacuum. The reaction afforded 2,2-ditetradecyl-1,3-propanediol in 91% yield 1H NMR (300 MHz, CDCl3): δ 3.57 (s, 4H, CH2O), 1.38-1.15 (m), 0.88 (t, 6H, J=8.0 Hz).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 2 h
  3. customThe reaction mixture is quenched with 1 M HCl solution
  4. extractionThe aqueous layer is extracted with diethyl ether two times
  5. washThe combined organic layers are washed with a dilute HCl solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customSolvents are evaporated under vacuum

Sources & evidence

ORD record
ord-6bc26c20adf046a2b04cfcc8e7a6ef4a
Source dataset
uspto-grants-2000_11
Patent number
US06153322

Reaction notes

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