Phenol → phenyl 4-nitrobenzenesulfonate

HRID 1764547Notes

Reaction equation

HRID 1764547 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[C:14]1([O:20][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 286918phenyl 4-nitrobenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 19.4 g amount of p-nitrobenzenesulfonyl chloride is added to 16.5 g of phenol in 80 ml of pyridine. The mixture is heated on a steam bath for one hour then is filtered and cooled to room temperature. The resulting yellow solution is poured into 300 ml of 10% aqueous sodium carbonate solution and stirred vigorously until the product is crystallized out. The solid is filtered, washed with water and dried, then is recrystallized from 300 ml of hot ethanol to give 20.0 g of 4-nitro-benzenesulfonic acid phenyl ester.

Workup

  1. temperatureThe mixture is heated on a steam bath for one hour
  2. filtrationthen is filtered
  3. additionThe resulting yellow solution is poured into 300 ml of 10% aqueous sodium carbonate solution
  4. customis crystallized out
  5. filtrationThe solid is filtered
  6. washwashed with water
  7. customdried
  8. customis recrystallized from 300 ml of hot ethanol

Sources & evidence

ORD record
ord-3052a188332e4e3abc3da2e3c85657d7
Source dataset
uspto-grants-1978_09
Patent number
US04117003

Reaction notes

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