Sodium Hydroxide → 1,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate (11.45 g, 29.5 mmol) was dissolved in ethanol (70 ml) and treated with sodium hydroxide (3.54 g, 88.5 mmol) dissolved in water (15 ml). This was heated at 60° C. under argon for 4 hours. The reaction was confirmed to be complete by LC/MS and thin layer chromatography. The reaction mixture was cooled to room temperature and evaporated to a third of the volume. This was acidified to pH2 with hydrochloric acid (2N) and extracted with ethyl acetate (3×100 ml). Combined organics washed with water, brine and dried over magnesium sulphate. Solvent was evaporated to give the title compound as a yellow solid (8.91 g, 26.8 mmol).

Provenance & Evidence