1-Naphthaldehyde → HCID 54004068, compound

HRID 1607393Notes

Reaction equation

HRID 1607393 reaction equation
C(O[C:4](=O)[CH2:5][CH2:6][C:7]([OH:9])=[O:8])C.[CH:11]1[CH:16]=[C:15]2[CH:17]=[CH:18][CH:19]=[C:20](C=O)[C:14]2=[CH:13][CH:12]=1.[H-].[Na+]>C(O)C>[C:16]1([CH:6]([CH:5]=[CH2:4])[C:7]([OH:9])=[O:8])[C:15]2[C:14](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 24758Sodium hydrideHCID 70610Monoethyl succinate

Product 1

HCID 54004068HCID 54004068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8.71 g of succinic acid ethyl ester and 7.81 g of 1-naphthylaldehyde in 50 ml of absolute ethanol was added 3.02 g of a 50% sodium hydride (suspension in oil) under ice-cooling, and then the mixture was heated under reflux for 3 hours. After cooling, the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether to remove neutral materials. The aqueous layer was acidified by adding concentrated hydrochloric acid and extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The ethereal solution was concentrated under reduced pressure to obtain 11.8 g of 3-ethoxycarbonyl-4-(1-naphthyl-3-butenoic acid as a yellow oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with diethyl ether
  8. customto remove neutral materials
  9. additionby adding concentrated hydrochloric acid
  10. extractionextracted with diethyl ether
  11. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationThe ethereal solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd78333c3c1f464b97e345d38a315e6e
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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