1-Naphthaldehyde → HCID 70048457, compound

Participants

Reaction Steps

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.

Provenance & Evidence