Ethyl Acetate → 2-Nonen-1-ol, (2E)-

HRID 1657943Notes

Reaction equation

HRID 1657943 reaction equation
[CH:1](=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>CCOCC>[CH2:1]([OH:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5283335(E)-2-NonenalHCID 21226445Aluminium lithium hydride

Product 1

HCID 53649412-Nonen-1-ol, (2E)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Trans-2-nonenal (7.0 g, 0.05 mole) is dissolved in 50 ml of ether and added to a solution of LiAlH4 (0.54 g, 0.014 mole) in 50 ml of ether at such a rate to maintain gentle refluxing. When the addition is complete, the solution is refluxed for one hour. Ethyl acetate (2 ml) is added to destroy excess LiAlH4. The mixture is acidified with 5M HCl. The ether layer is separated, washed 2X with water, and dried over sodium sulfate. The ether solution is concentrated and the residue vacuum distilled to yield trans-2-nonenol.

Workup

  1. temperatureto maintain gentle refluxing
  2. additionWhen the addition
  3. temperaturethe solution is refluxed for one hour
  4. customto destroy excess LiAlH4
  5. customThe ether layer is separated
  6. washwashed 2X with water
  7. dry with materialdried over sodium sulfate
  8. concentrationThe ether solution is concentrated
  9. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-e9eb87aa9e67405796f2ad3ab25ce349
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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