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

HRID 542366Notes

Reaction equation

HRID 542366 reaction equation
[C:1]([O:10]CC)(=[O:9])[CH2:2][CH2:3][C:4]([O:6]CC)=[O:5].[C:13]1([CH:23]=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[OH-].[Na+]>C(O)C>[C:13]1([CH:23]=[C:3]([CH2:2][C:1]([OH:10])=[O:9])[C:4]([OH:6])=[O:5])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 31249Diethyl Succinate

Product 1

HCID 541426892-[(Naphthalen-1-yl)methylidene]butanedioic acidYield 55.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 32.3 g of diethyl succinate and 29.0 g of 1-naphthaldehyde in 100 ml of absolute ethanol was added 10.7 g of sodium hydride (50% dispersion in mineral oil) under ice-cooling, and then the mixture was heated under reflux for 0.5 hours. To the reaction was added 230 ml of 1N-aqueous sodium hydroxide solution, and the mixture was heated under reflux for 1 hour. The reaction mixture was evaporated under reduced pressure, and water was added to the residue. The mixture was extracted with diethyl ether to remove neutral substances. The aqueous layer was acidified by adding concentrated hydrochloric acid, and extracted with diethyl ether. The ethereal layer was washed a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. Benzene was added to the residue, and the precipitated crystals were collected by flitration 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 0.5 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1 hour
  6. customThe reaction mixture was evaporated under reduced pressure, and water
  7. additionwas added to the residue
  8. extractionThe mixture was extracted with diethyl ether
  9. customto remove neutral substances
  10. additionby adding concentrated hydrochloric acid
  11. extractionextracted with diethyl ether
  12. washThe ethereal layer was washed a saturated sodium chloride aqueous solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customevaporated under reduced pressure
  15. additionBenzene was added to the residue
  16. customthe precipitated crystals were collected by flitration

Sources & evidence

ORD record
ord-37a65d9eb926414096b08f42bc3db9f3
Source dataset
uspto-grants-1987_04
Patent number
US04656269

Reaction notes

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