Phenol → Phenyl 2,4-dichloro-3-nitrobenzenesulfonate

HRID 840568

Reaction equation

HRID 840568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N+:9]([O-:11])=[O:10].Cl[S:13]([OH:16])(=[O:15])=[O:14].[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>CC(C)=O.O>[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:8])[CH:5]=[CH:6][C:7]=1[S:13]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 117591,3-Dichloro-2-nitrobenzeneHCID 24638Chlorosulfonic acid2×

Product 1

HCID 22619793Phenyl 2,4-dichloro-3-nitrobenzenesulfonate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2,6-Dichloronitrobenzene was stirred for 7 hours at 130° C. with an excess of chlorosulfonic acid. After cooling, the mixture was poured onto ice, the sulfochloride was filtered off with suction, washed to neutrality and dried over sodium hydroxide, melting point 91° C. The resulting sulfochloride (29.05 g, 0.1 mol) and phenol (11.5 g, 0.12 mol) were dissolved in 150 ml of acetone and treated with 14 ml of triethylamine at 10° C. The mixture was stirred for 1 hour with cooling, stirring was then continued for a further 4 hours at room temperature, the mixture was then treated with 200 ml of water, the resulting precipitate was filtered off with suction at 10° C., washed with water and dried in vacuo at 80° C., melting point 102° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice
  3. filtrationthe sulfochloride was filtered off with suction
  4. washwashed to neutrality
  5. dry with materialdried over sodium hydroxide, melting point 91° C
  6. temperaturewith cooling
  7. stirringstirring
  8. waitwas then continued for a further 4 hours at room temperature
  9. filtrationthe resulting precipitate was filtered off with suction at 10° C.
  10. washwashed with water
  11. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-234ce935a86f4124aff4fc9e10c4bde2
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Linked notes

Loading…