Ethyl Acetate → (E,E)-4-ethyl-2,4-heptadien-1-ol

HRID 2396911Notes

Reaction equation

HRID 2396911 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7](/[C:9](=[CH:16]\[CH2:17][CH3:18])/[CH:10]=[CH:11]/[C:12](OC)=[O:13])[CH3:8].C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH2:7](/[C:9](=[CH:16]\[CH2:17][CH3:18])/[CH:10]=[CH:11]/[CH2:12][OH:13])[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 12700325methyl (E,E)-4-ethyl-2,4-heptadienoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 86749298(E,E)-4-ethyl-2,4-heptadien-1-olYield 91.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.38 g) in ethyl ether (160 ml) was added a solution of methyl (E,E)-4-ethyl-2,4-heptadienoate (13.2 g) in ethyl ether (100 ml) while keeping the temperature below 30° C. When addition was completed, the mixture was allowed to stir at room temperature for one hour. To this resultant mixture at 10° C. were added dropwise ethyl acetate (50 ml) and a saturated aqueous solution of potassium sodium tartrate (50 ml). The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give (E,E)-4-ethyl-2,4-heptadien-1-ol (10.1 g) as an oil. This oil was used in the next reaction without further purification.

Workup

  1. customthe temperature below 30° C
  2. additionWhen addition
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b083db324f7e4754b20565b7fe13c692
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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