1-Naphthaldehyde → 2-[(Naphthalen-1-yl)methylidene]butanedioic acid

HRID 1722179Notes

Reaction equation

HRID 1722179 reaction equation
[C:1]([O:8]CC)(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=[O:5].[C:11]1([CH:21]=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[H-].[Na+].[OH-].[Na+]>C(O)C>[C:11]1([CH:21]=[C:3]([CH2:2][C:1]([OH:8])=[O:7])[C:4]([OH:6])=[O:5])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 17119674-Ethoxy-4-oxobutanoate

Product 1

HCID 541426892-[(Naphthalen-1-yl)methylidene]butanedioic acidYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 32.3 g of ethyl succinate and 29.0 g of 1-naphthaldehyde in 320 ml of an absolute ethyl alcohol was added 10.7 g of a 50% sodium hydride (dispersion in mineral oil) under ice-cooling, and the mixture was heated under reflux for 30 minutes. To the reaction mixture was added 230 ml of a 1N-aqueous sodium hydroxide solution, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl ether to remove neutral materials. The aqueous layer was acidified with a concentrated hydrochloric acid, and extracted with ethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. To the residue was added benzene, and precipitated crystals were collected by filtration to obtain 26.5 g of 2-(1-naphthylmethylene) succinic acid as yellow crystals.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionTo the residue was added water
  6. extractionthe mixture was extracted with ethyl ether
  7. customto remove neutral materials
  8. extractionextracted with ethyl ether
  9. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. additionTo the residue was added benzene
  13. customprecipitated crystals
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-284c3f85828b4cb29e4d833df2777614
Source dataset
uspto-grants-1989_08
Patent number
US04853463

Reaction notes

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