Methanol → HCID 18972854, compound

In a 2-liter round-bottomed flask were placed methyl 4-amino-5-chloro-3-methylsulfonyloxybenzoate (8.7 g, 31.1 mmole), 50% aqueous sodium hydroxide (10.1 g, 126 mmole), methanol (250 ml) and water (550 ml). The resulting mixture was refluxed for 3 hours. The reaction mixture was cooled down to room temperature and poured into a mixture of water and ethyl acetate. The aqueous layer was separated, neutralized to pH 6 with concentrated aqueous hydrochloric acid, and extracted with ethyl acetate (3×400 ml). The combined organic layers were washed with water (2×200 ml), dried over anhydrous magnesium sulfate and the solvent eliminated in the rotary evaporator yielding 4.3 g of the expected 4-amino-5-chloro-3-hydroxybenzoic acid (intermediate XII). (1H-NMR, DMSO-d6 12.5(1,bs); 10(1,bs); 7.22(1,s); 5.4(2,s))

1. customIn a 2-liter round-bottomed flask were placed
2. temperatureThe resulting mixture was refluxed for 3 hours
3. customThe aqueous layer was separated
4. extractionextracted with ethyl acetate (3×400 ml)
5. washThe combined organic layers were washed with water (2×200 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent eliminated in the rotary evaporator

ORD record

ord-9948d0e6345d4ffaa3670c839b25847d

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811427