Diethyl 2,2-dihexylmalonate → 2,2-Dihexylpropane-1,3-diol

HRID 70754Notes

Reaction equation

HRID 70754 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:12](OCC)=[O:13])C>C1COCC1>[CH2:23]([C:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH2:10][OH:9])[CH2:12][OH:13])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 599758Diethyl 2,2-dihexylmalonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 227192912,2-Dihexylpropane-1,3-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (LAH) (2 g, 52.6 mmol) in dry THF (20 mL) was stirred at room temperature, and a THF solution of substituted malonic acid diethyl ester (26.3 mmol, (5)) was added dropwise. The reaction was allowed to reflux for 3 h and was quenched by the addition of cold water. The compound was extracted in ethyl acetate. The organic layer was washed with water, dried over Na2SO4, and evaporated to produce the product (6) as either a sticky liquid or a low-melting solid.

Workup

  1. temperatureto reflux for 3 h
  2. customwas quenched by the addition of cold water
  3. extractionThe compound was extracted in ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-64fc795d7941443292bd453da98fec03
Source dataset
uspto-grants-2014_09
Patent number
US08822635B2

Reaction notes

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