Hydrochloric Acid → 1-(2,4-Dihydroxy-3-nitrophenyl)ethan-1-one

Temperature

5 °C

The extraction solvent can be changed from diethyl ether to di-isopropyl ether. For example: Nitrobenzene (87.5 mL) was added to aluminium trichloride (46.33 g). 2-nitroresorcinol (25 g), in nitrobenzene (112.5 mL) was added. The mixture was cooled to 5° C. and acetic acid anhydride (15.68 mL) added maintaining the internal temperature below 20° C. The mixture was heated to 100° C. for 2 h then cooled to 5° C. Cold (3° C.) 3M aqueous hydrogen chloride (200 mL) was charged. The mixture was heated to 20° C. then di-isopropylether (200 mL) charged. The aqueous phase was removed and the organic phase extracted with 2 M aqueous sodium hydroxide (200 mL). The aqueous phase was washed with di-isopropylether (200 mL). The aqueous phase was removed and heated to 50° C. 3 M aqueous hydrogen chloride (467.5 mL) was charged and the mixture cooled to 20° C. The suspension was filtered, washed with water (50 mL) and dried under vacuum to yield the title compound (31.14 g).

1. temperaturemaintaining the internal temperature below 20° C
2. temperatureThe mixture was heated to 100° C. for 2 h
3. temperaturethen cooled to 5° C
4. temperatureThe mixture was heated to 20° C.
5. customThe aqueous phase was removed
6. extractionthe organic phase extracted with 2 M aqueous sodium hydroxide (200 mL)
7. washThe aqueous phase was washed with di-isopropylether (200 mL)
8. customThe aqueous phase was removed
9. temperatureheated to 50° C
10. addition3 M aqueous hydrogen chloride (467.5 mL) was charged
11. temperaturethe mixture cooled to 20° C
12. filtrationThe suspension was filtered
13. washwashed with water (50 mL)
14. customdried under vacuum

ORD record

ord-6ed989f2501242b8aa3f5d608df6c9f2

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017602B2