Sodium Hydroxide → 1,4-Diethoxynaphthalene-2,3-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Diethyl 1,4-bis(ethyloxy)-2,3-naphthalenedicarboxylate (24.8 g, 68.8 mmol) was suspended in ethanol (200 ml) and treated with sodium hydroxide (8.3 g, 206.4 mmol) dissolved in 200 ml of water. A further 50 ml of ethanol added to aid stirring. Heated to reflux, 100° C. All in solution on heating. Refluxed for 8 hours. Cooled to room temperature and stood overnight. Solvent was evaporated to almost dryness. Water was added and stirred in an ice bath. Acidified with 2M HCl solution (˜150 ml). The white precipitate was filtered, washed with water and dried in a vacuum oven to give the title compound as a white solid (18.77 g, 61.7 mmol).

Provenance & Evidence