Sulfuric Acid → HCID 83681099, compound

Temperature

2.5 °C

A solution of 3-chloro-2-methoxy-4-nitrotoluene (1.0 g, 5.0 mmol) in acetic acid (10 mL) and acetic anhydride (10 mL) was cooled to 5° C. and treated with 1 mL conc. H2SO4. Chromium trioxide (1.4 g, 14 mmol) was added in portions over 10 minutes while the reaction temperature was maintained at 0-5° C. After 30 minutes at this temperature, the mixture was poured onto ice-water (20 g) and the mixture was extracted with ethyl acetate (2×25 mL). The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated. The crude bis-acetate was combined with water (10 mL), ethanol (10 mL) and concentrated sulfuric acid (1 mL) and heated to reflux for 40 minutes. Upon cooling, the mixture was diluted with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine, dried (sodium sulfate) and concentrated. The crude mixture was chromatographed (10% ethyl acetate/hexanes) to give 3-chloro-2-methoxy-4-nitrobenzaldehyde (400 mg, 1.9 mmol): LC/MS (m/z=215).

1. additionthe mixture was poured onto ice-water (20 g)
2. extractionthe mixture was extracted with ethyl acetate (2×25 mL)
3. washThe combined organic phases were washed with brine
4. dry with materialdried (sodium sulfate)
5. concentrationconcentrated
6. temperatureheated
7. temperatureto reflux for 40 minutes
8. temperatureUpon cooling
9. additionthe mixture was diluted with water (20 mL)
10. extractionextracted with ethyl acetate (2×50 mL)
11. washThe combined extracts were washed with brine
12. dry with materialdried (sodium sulfate)
13. concentrationconcentrated
14. customThe crude mixture was chromatographed (10% ethyl acetate/hexanes)

ORD record

ord-fcd268e8de5b42bc95b56204352314a9

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07498468B2