Nitric Acid → HCID 20291119, compound

HRID 1413865Notes

Reaction equation

HRID 1413865 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:22])=[C:10]([C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[OH:21])=[O:13])[CH:11]=1>C(O)(=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([N+:1]([O-:4])=[O:2])[C:9]([OH:22])=[C:10]([C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[OH:21])=[O:13])[CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 18919733HCID 18919733, compound

Product 1

HCID 20291119HCID 20291119, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (4 ml) was added dropwise to a stirred solution of bis(5-chloro-2-hydroxyphenyl)ketone (2.7 g) in glacial acetic acid (50 ml). The solution was stirred at room temperature for 1 hr and during this time a yellow solid separated from solution. The mixture was poured into ice water and the product collected by filtration. Thin layer chromatography indicated that the product was a mixture of two compounds which were separated by column chromatography on silica gel. Elution with hexane containing increasing amounts of ethyl acetate afforded 5-chloro-2-hydroxyphenyl 5-chloro-2-hydroxy-3-nitrophenyl ketone (150 mg) m.p. 153° C., followed by bis-(5-chloro-2-hydroxy-3-nitrophenyl)ketone (1.5 g), m.p. 187° C.

Workup

  1. customseparated from solution
  2. additionThe mixture was poured into ice water
  3. filtrationthe product collected by filtration
  4. additiona mixture of two compounds which
  5. customwere separated by column chromatography on silica gel
  6. washElution with hexane containing
  7. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-2d77e278393a46a4b9006a3b13dd254e
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

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