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

HRID 1722901Notes

Reaction equation

HRID 1722901 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 absolute ethyl alcohol was added 10.7 g of a 50% sodium hydride (dispersion in mineral oil), and the mixture was heated under reflux for 0.5 hours. To the reaction mixture was added 230 ml of a 1N-aqueous sodium hydroxide solution, and the mixture was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with diethyl ether to remove neutral materials. The aqueous layer was acidified by the addition of concentrated hydrochloric acid, and the acid solution was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated 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.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 0.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. extractionthe residue was extracted with diethyl ether
  7. customto remove neutral materials
  8. additionThe aqueous layer was acidified by the addition of concentrated hydrochloric acid
  9. extractionthe acid solution was extracted with diethyl ether
  10. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. additionTo the residue was added benzene
  14. customprecipitated crystals
  15. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-10e862f04d174c4c9e4fb15697280053
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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