(E)-2-Nonenoic Acid → 2-Nonen-1-ol, (2E)-

HRID 1657944Notes

Reaction equation

HRID 1657944 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7](O)(=[O:16])/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>CCOCC>[CH2:7]([OH:16])/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 5312586(E)-2-Nonenoic AcidHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 500 ml flask with a reflux condenser, mechanical stirrer and a dropping funnel, and protected from moisture with a drying tube is charged with LiAlH4 (6.1 g, 0.16 mole) and 200 ml ether. A solution of trans-2-nonenoic acid (7.8 g, 0.05 mole) in 25 ml ether is added at a rate to maintain refluxing. Refluxing is continued for 1 hour and the mixture cooled. Exess reagent is destroyed by the addition of ethyl acetate (5 ml) followed by acidification with 5M HCl. The organic layer is separated, washed with water, dried and distilled under vacuum to give trans-2-nonenol.

Workup

  1. customA 500 ml flask with a reflux condenser, mechanical stirrer and a dropping funnel, and protected from moisture with a drying tube
  2. temperatureto maintain
  3. temperaturerefluxing
  4. temperatureRefluxing
  5. temperaturethe mixture cooled
  6. customExess reagent is destroyed by the addition of ethyl acetate (5 ml)
  7. customThe organic layer is separated
  8. washwashed with water
  9. customdried
  10. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-885c5416208049a48577fb256c5ab3b5
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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