Nitric Acid → 4-Chloro-2-nitro-1-naphthol

4-Chloro-1-naphthol, 9 g, in 100 ml acetic acid was cooled to 15° C. and 3.25 ml concentrated nitric acid in 20 ml acetic acid was added dropwise over 15 minutes. After 1 hour, the reaction mixture was poured into 600 ml chilled water. The precipitate was filtered off, washed with water and dried to give a crude product. The product was partially purified by extracting with boiling hexane to obtain 3.5 g. Further purification was accomplished by dissolving in 10 ml chloroform, absorbing on 15 g silica and loading on a column of 90 g silica gel, equilibrated with hexane. The product was eluted with 5% ethyl acetate in hexane to give 0.8 g of 4-chloro-2-nitro-1-naphthol after evaporation, m.p. 142°-3° (d).

1. additionthe reaction mixture was poured into 600 ml
2. filtrationThe precipitate was filtered off
3. washwashed with water
4. customdried
5. customto give a crude product
6. customThe product was partially purified
7. extractionby extracting with boiling hexane
8. customto obtain 3.5 g
9. customFurther purification
10. dissolutionby dissolving in 10 ml chloroform
11. customabsorbing on 15 g silica and loading on a column of 90 g silica gel
12. washThe product was eluted with 5% ethyl acetate in hexane

ORD record

ord-075133fccd6e4eb6bc7c41a53f206b5f

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04963479