Sodium Hydroxide → 3-Benzyloxy-5-methoxy-4-nitrophenoxyacetic acid

Participants

Reaction Steps

In ethanol (50 ml) was dissolved methyl 3-benzyloxy-5-methoxy-4-nitrophenoxyacetate (1.53 g, 4.41 mmol), followed by the addition of 5% palladium/carbon (1 g). At room temperature and normal pressure, the mixture was subjected to catalytic hydrogenation for 15 hours. The reaction mixture was filtered through Celite under reduced pressure to remove the insoluble matter. The filtrate was stirred at room temperature. To the filtrate was added 2-tolyl isothiocyanate (711 μl, 5.29 mmol). After stirring at room temperature for 15 hours, mercuric oxide (yellow) (1.62 g, 7.50 mmol) was added and the mixture was heated and refluxed for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite under reduced pressure to remove the insoluble matter. The filtrate was then distilled under reduced pressure to remove the solvent. The resulting oily residue was dissolved in THF (35 ml). To the solution was added 0.25N NaOH (35 ml, 8.75 mmol) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was poured in 1N HCl (100 ml), followed by extraction with a chloroform-methanol (4:1, 2×200 ml) mixture. The extract was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. Chloroform-hexane was added to the residue to crystallize the same, whereby the title compound (487 mg, 34%) was obtained as a pale yellow amorphous substance.

Provenance & Evidence