ethyl 2-((E)-4-methoxybenzylidene)butyrate → HCID 14329809, compound

HRID 35577Notes

Reaction equation

HRID 35577 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12](/[CH:13]=[C:14](\[CH2:20][CH3:21])/[C:15](OCC)=[O:16])=[CH:11][CH:10]=1>CCOCC>[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12](/[CH:13]=[C:14](\[CH2:20][CH3:21])/[CH2:15][OH:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10933410ethyl 2-((E)-4-methoxybenzylidene)butyrateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 14329809HCID 14329809, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of lithium aluminum hydride (3 g) in dry ether (300 ml) was added a solution of ethyl 2-((E)-4-methoxybenzylidene)butyrate (19 g) in dry ether (30 ml) at 0° C. with stirring. The mixture was stirred at the same temperature for 3 hours and excess lithium aluminum hydride was decomposed with wet ether. The reaction mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and then evaporated to dryness to give 2-((E)-4-methoxybenzylidene)butan-1-ol (13 g).

Workup

  1. stirringThe mixture was stirred at the same temperature for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c2a023fb300944d39deb4e99c77ecce6
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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