1-Naphthaldehyde → HCID 70048457, compound

HRID 1768576Notes

Reaction equation

HRID 1768576 reaction equation
[H-].[Na+].[C:3]([O:13]C)(=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]C)=[O:9].[C:15]1(C=O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>CO>[C:23]1(=[C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:13])=[O:12])[C:8]([OH:10])=[O:9])[C:24]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][CH2:22]1

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 12329DimethyladipateHCID 14798Sodium HydroxideHCID 24758Sodium hydride

Product 1

HCID 70048457HCID 70048457, compoundYield 34,766.102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.96 g (0.18 mmole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 26.4 g (0.15 mmole) of dimethyl adipate and 23.7 g (0.15 mmole) of 1-naphthaldehyde dissolved in 200 ml of anhydrous methanol, and the mixture was heated under reflux for 30 minutes. At the end of this time, 150 ml (0.15 mole) of a 1N aqueous solution of sodium hydroxide were added to the solution, and the mixture was heated under reflux for 1 hour. The solvent was then removed by distillation under reduced pressure, and the residue was mixed with water and then washed with diethyl ether. The aqueous layer was acidified and extracted with diethyl ether. The ethereal extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and residue was triturated with diisopropyl ether to precipitate crystals, which were collected by filtration to afford 14.2 g of 2-(1-naphthylidene)adipic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hour
  5. customThe solvent was then removed by distillation under reduced pressure
  6. additionthe residue was mixed with water
  7. washwashed with diethyl ether
  8. extractionextracted with diethyl ether
  9. extractionThe ethereal extract
  10. washwas washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure, and residue
  13. customwas triturated with diisopropyl ether
  14. customto precipitate crystals, which
  15. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-987098ab5f204beba4af57a52e668f0a
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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