Ethyl Acetate → HCID 53661256, compound

HRID 2396902Notes

Reaction equation

HRID 2396902 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7](/[C:9](=[CH:16]\[CH:17]([CH3:19])[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][CH:17]([CH3:18])[CH3:19])[CH:10]=[CH:11][CH2:12][OH:13])[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86749294HCID 86749294, compound

Product 1

HCID 53661256HCID 53661256, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (5.41 g) in ethyl ether (550 ml) was added a solution of methyl (E,E)-4-ethyl-6-methyl-2,4-heptadienoate (35 g) in ethyl ether 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 (100 ml) and a saturated solution of potassium sodium tartrate (50 ml). The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give 4-ethyl-6-methyl-2,4-heptadiene-1-ol (23.98 g) as an oil.

Workup

  1. customthe temperature below 30° C
  2. additionWhen addition
  3. customat 10° C
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c238deb1b9164792af8c05f8609498e7
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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