Hydrochloric Acid → 2,6-Dichloro-4-nitrophenol

HRID 1638440Notes

Reaction equation

HRID 1638440 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[ClH:11].[Cl:12]Cl.[N+](C1C=CC=CC=1O)([O-])=O>O>[Cl:11][C:4]1[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[CH:1]=[C:2]([Cl:12])[C:3]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 9804-Nitrophenol2×HCID 69472-NitrophenolHCID 24526Chlorine3×

Product 1

HCID 120662,6-Dichloro-4-nitrophenolYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

139 parts of p-nitrophenol are suspended in 292 parts of water and the suspension is ground. A reactor is then charged with 1250 parts of 20 % hydrochloric acid which has been used as reaction medium for a previous batch and recycled to the reactor after isolation of the product. Then 156 parts of chlorine and the suspension of p-nitrophenol are added simultaneously at 25° C. to the hydrochloric acid. The suspension of nitrophenol is added over 240 minutes, whereas the simultaneous addition of chlorine is made for 20 minutes longer over 260 minutes. The batch is then allowed to react for 30 minutes and excess chlorine is expelled over a further 30 minutes. The product is isolated by filtration, washed until neutral and dried, affording 200 parts of 2,6-dichloro-4-nitrophenol (corresponding to a yield of 96 %). Melting point: 119°-120° C. (lit.: 125° C.).

Workup

  1. customhas been used as reaction medium for a previous batch and recycled to the reactor after isolation of the product
  2. customto react for 30 minutes
  3. customThe product is isolated by filtration
  4. washwashed until neutral and
  5. customdried

Sources & evidence

ORD record
ord-2fa84771a54142dba3b64cc5ed0034e8
Source dataset
uspto-grants-1989_11
Patent number
US04879415

Reaction notes

Loading…