Acetic Anhydride → 1-(2,4-Dihydroxy-3-nitrophenyl)ethan-1-one

Temperature

100 °C

2-Nitrobenzene-1,3-diol (24.5 g) was added portionwise over 15 minutes to a vigorously stirred solution of aluminum chloride (46.3 g) in nitrobenzene (325 mL). Acetic anhydride (15.7 mL) was then added dropwise to the mixture over a further 15 minutes and the mixture then heated at 100° C. for 5 h. The reaction was cooled to ambient temperature and carefully quenched with ice cold 2M hydrochloric acid (300 mL). The mixture was extracted with diethyl ether (2×500 mL) and the combined diethyl ether extracts then extracted with 2M aqueous sodium hydroxide (2×400 mL). The combined basic extracts were washed with diethyl ether (4×500 mL) and then acidified to pH 1 with 2M hydrochloric acid (700 mL). The resulting precipitate was filtered off, washed with water, and dried under vacuum at 40° C. to afford the subtitled compound as a yellow-brown solid. Yield 29.5 g.

1. temperatureThe reaction was cooled to ambient temperature
2. customcarefully quenched with ice cold 2M hydrochloric acid (300 mL)
3. extractionThe mixture was extracted with diethyl ether (2×500 mL)
4. extractionthe combined diethyl ether extracts then extracted with 2M aqueous sodium hydroxide (2×400 mL)
5. washThe combined basic extracts were washed with diethyl ether (4×500 mL)
6. filtrationThe resulting precipitate was filtered off
7. washwashed with water
8. customdried under vacuum at 40° C.

ORD record

ord-e59c0784c5084ab0ad9fc37d8f465bff

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2