Hydrochloric Acid → 3,5-Dimethyl-4-nitrophenol

Formation of compound (b): To a mixture of 3,5-dimethylphenol (a) (25 g, 205 mmol) and NaNO3 (26.1 g, 307 mmol) in ether (200 mL) and water (200 mL), at 0° C., 250 mL of conc.HCl solution was added dropwise within 1 hour under stirring. The reaction mixture was kept under stirring overnight and the temperature was allowed to warm to room temperature. The organic phase was seperated and the aqueous phase was extracted with ether (3×100 mL). The combined organic phase was washed with 3N HCl (2×100 mL), saturated NaHCO3 solution (3×100 mL) and finally with brine (200 mL), dried over Na2SO4, filtered and concentrated to dryness. The obtained residue was purified by chromatography over silica gel by using ethyl acetate and hexane (2:8) as eluent. The collected fractions were further recrystalized in ether/hexane to afford compound (b), 3,5-dimethyl-4-nitrophenol (6.7 g, 19% yield) as a yellow solid. MS: m/e 167

1. customat 0° C.
2. stirringunder stirring overnight
3. customThe organic phase was seperated
4. extractionthe aqueous phase was extracted with ether (3×100 mL)
5. washThe combined organic phase was washed with 3N HCl (2×100 mL), saturated NaHCO3 solution (3×100 mL) and finally with brine (200 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe obtained residue was purified by chromatography over silica gel
10. customThe collected fractions were further recrystalized in ether/hexane

ORD record

ord-4600b6cb4a8a4b92beb0ccb10567a2c0

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495681B1