Water → Phenyl 4-chloro-3-nitrobenzenesulfonate

HRID 1834218

Reaction equation

HRID 1834218 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-:3])=[O:2].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>CC(C)=O>[C:15]1([O:21][S:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)(=[O:12])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8471Triethylamine

Product 1

HCID 266121Phenyl 4-chloro-3-nitrobenzenesulfonateYield 86.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Nitro-4-Chloro-benzene-sulfonic acid-phenylester was obtained by mixing 51 g of 3-nitro-4-chloro-benzene-sulfonic acid-chloride with 18.8 g of phenol in 120 ml of acetone, and by adding 28 ml of triethylamine dropwise, while cooling, at a temperature not exceeding 10° C. The mixture was continued to be stirred for several hours at room temperature, and then water was added, in which process an oil was separated which was extracted with ether. After recrystallization of the residue from methanol, 54 g of 3-nitro-4-chloro-benzene-sulfonic acid-phenylester were obtained, which had a melting point of 71° C.

Workup

  1. temperaturewhile cooling, at a temperature not
  2. customexceeding 10° C
  3. customwas separated which
  4. extractionwas extracted with ether
  5. customAfter recrystallization of the residue from methanol

Sources & evidence

ORD record
ord-68f9f87caa824dce93a2d5dd5a4266ed
Source dataset
uspto-grants-1978_01
Patent number
US04069325

Linked notes

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