1-Naphthaldehyde → 3-Ethoxycarbonyl-4-(1-naphthyl)-3-butenoic acid

HRID 1905309Notes

Reaction equation

HRID 1905309 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[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+]>C(O)C>[CH2:9]([O:8][C:1]([C:2](=[CH:21][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([OH:6])=[O:5])=[O:7])[CH3:10]

Participants

5

Reactant 3

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

Product 1

HCID 540390073-Ethoxycarbonyl-4-(1-naphthyl)-3-butenoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 17.40 g of ethyl succinate and 15.62 g of 1-naphthaldehyde in 100 ml of absolute ethanol was added 6.00 g of sodium hydride (50% dispersion in mineral oil), and the mixture was heated under reflux for 3 hours. 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 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, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 23.60 g of 3-ethoxycarbonyl-4-(1-naphthyl)-3-butenoic acid as a yellow oil. A mixture of 200 ml of a 1N-aqueous sodium hydroxide solution and 170 ml of ethanol was added to 23.50 g of the butenoic acid obtained. The mixture was heated at 50° C. for 1.5 hours. 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 materials. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 15.30 g of 2-(1-naphthylmethylene)succinic acid as yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction mixture was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with diethyl ether
  6. customto remove neutral materials
  7. additionby adding concentrated hydrochloric acid
  8. extractionextracted with diethyl 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

Sources & evidence

ORD record
ord-d9cbc7927caa4a0390335dbd5bfce0cb
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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