Hydrochloric Acid → Phenol, 5-chloro-2-nitro-

HRID 483912Notes

Reaction equation

HRID 483912 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH-:12].[Na+].Cl>O>[N+:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[OH:12])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 118992,4-DichloronitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 11900Phenol, 5-chloro-2-nitro-Yield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

192.0 g (1 mol) of 2,4-dichloronitrobenzene, 600 g of water and 273.0 g (2.05 mol) of sodium hydroxide are heated to 140° C. in a VA steel autoclave with vigorous stirring for 6 hours. The reacted reaction mixture is removed from the autoclave at 70° C. The orange-brown solution produced is adjusted to pH 2 using 30% strength hydrochloric acid, and the product is distilled over using steam. On stirring the distillate (about 1.5 1) at 10° C, 2-nitro-5-chlorophenol (156.4 g, 90% of theory) is obtained in the form of yellow crystals.

Workup

  1. customThe reacted reaction mixture
  2. customis removed from the autoclave at 70° C
  3. customThe orange-brown solution produced
  4. distillationthe product is distilled
  5. stirringOn stirring the distillate (about 1.5 1) at 10° C

Sources & evidence

ORD record
ord-abc0a16acb984a0898d56f7dbae0f885
Source dataset
uspto-grants-1993_07
Patent number
US05227535

Reaction notes

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