Hydrochloric Acid → Methyl 3-hydroxy-4-nitrobenzoate

In a 1 liter round-bottomed flask were placed 25 g (0.14 mole) 3-hydroxy-4-nitrobenzoic acid, 37% hydrochloric acid (37 ml) and methanol (300 ml). The resulting mixture was refluxed for 10 hours. The reaction mixture was cooled to room temperature and the solvent eliminated in a rotary evaporator. The resulting residue was dissolved in ethyl acetate and washed sequentially with water (1×100 ml), aqueous sodium bicarbonate (1×100 ml), water (1×100 ml) and brine (1×100 ml). The organic layer was dried over anhydrous magnesium sulfate and solvent was removed in the rotary evaporator, yielding 22.5 g of the expected methyl 3-hydroxy-4-nitrobenzoate as a yellow solid which was used as such in the next step.

1. customIn a 1 liter round-bottomed flask were placed
2. temperatureThe resulting mixture was refluxed for 10 hours
3. customthe solvent eliminated in a rotary evaporator
4. dissolutionThe resulting residue was dissolved in ethyl acetate
5. washwashed sequentially with water (1×100 ml), aqueous sodium bicarbonate (1×100 ml), water (1×100 ml) and brine (1×100 ml)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and solvent
7. customwas removed in the rotary evaporator

ORD record

ord-036caa3cb94e4dd09b47890d7cf767c8

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811427