Réaction #43992

Équation de réaction

Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate

sodium hydroxide

→

1,4-diethoxy-2,3-naphthalenedicarboxylic acid

Rendement 92.3%

Solvants

ethanol

water

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was cooled
2. 2
   Filtrationthe thick white suspension was filtered
3. 3
   workup.DISSOLUTIONThe solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml)
4. 4
   AutreThe layers were separated
5. 5
   ExtractionThe aqueous was extracted with ethyl acetate (2×)
6. 6
   Séchagethe combined organics were dried (MgSO4)
7. 7
   AutreEvaporation of the solvent under vacuum

Mode opératoire

Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate (32 g, 89 mmol) was added to a solution of sodium hydroxide (20 g) in ethanol (200 ml) and water (40 ml) and stirred for 1.5 h at 60° C. The reaction was cooled and the thick white suspension was filtered. The solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml). The layers were separated and the aqueous was acidified with hydrochloric acid (2M, 120 ml). The aqueous was extracted with ethyl acetate (2×) and the combined organics were dried (MgSO4). Evaporation of the solvent under vacuum gave 1,4-diethoxy-2,3-naphthalenedicarboxylic acid as a white solid (25 g, 92%).

Source