Nitric Acid → 3-Chloro-4-nitrophenol

HRID 1451635Notes

Reaction equation

HRID 1451635 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1>C(O)(=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 79333-Chlorophenol

Product 1

HCID 102833-Chloro-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Concentrated nitric acid (10 ml) in acetic acid (30 ml) was added dropwise to a cooled solution of 3-chlorophenol (10 g) in acetic acid (10 ml). After 1 hour at -5°, the mixture was poured onto ice, extracted with ether, dried over sodium sulfate and evaporated. The residue was then pun fled by column chromatography eluting with hexane-ethyl acetate (85:15) to give the title compound (9 g). M.p. 120°.

Workup

  1. additionthe mixture was poured onto ice
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. washeluting with hexane-ethyl acetate (85:15)

Sources & evidence

ORD record
ord-ec4b01ff94e047cc9ba4ccb8c1c25bee
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

Loading…