Hydrochloric Acid → 2-Chloro-4,6-dinitrophenol

HRID 1638441

Reaction equation

HRID 1638441 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].[N+](C1C([N+]([O-])=O)=C(O)C=CC=1)([O-])=O.[ClH:27].ClCl>O>[Cl:27][C:6]1[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[OH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14932,4-Dinitrophenol2×HCID 61912,3-Dinitrophenol2×HCID 24526Chlorine3×

Product 1

HCID 136812-Chloro-4,6-dinitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

160 parts of 2,4-dinitrophenol are suspended in 240 parts of water. Then 0.5 part of lignosulfonate (dispersant) is added to this suspension and the dinitrophenol is comminuted by ultrasonication. A reactor is charged with 210 parts of 14 % hydrochloric acid and the aqueous suspension of finely particulate 2,4-dinitrophenol and 60 parts of chlorine gas are added simultaneously at 0° C. The addition of the suspension of dinitrophenol is made over 120 minutes and the chlorine is simultaneously added over 130 minutes. When the addition of chlorine is complete, the product is isolated by filtration and washed with 250 parts of water, affording 162.4 parts of 2-chloro-4,6-dinitrophenol (corresponding to a yield of c. 83 %).

Workup

  1. additionare added simultaneously at 0° C
  2. customthe product is isolated by filtration
  3. washwashed with 250 parts of water

Sources & evidence

ORD record
ord-59ea38ec3eec4a408172e25edbc08f1e
Source dataset
uspto-grants-1989_11
Patent number
US04879415

Linked notes

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