2-Nitroanisole → Benzenesulfonyl chloride, 4-methoxy-3-nitro-

HRID 2057574Notes

Reaction equation

HRID 2057574 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])([O-:8])=[O:7]>>[CH3:16][O:15][C:10]1[C:9]([N+:6]([O-:8])=[O:7])=[CH:14][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 70482-NitroanisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 89600Benzenesulfonyl chloride, 4-methoxy-3-nitro-

Conditions

Temperature
0 °C

Procedure

2.5 mols (165 ml) of chlorosulphonic acid are placed in a one-liter reaction vessel equipped with a stirring system, a thermometer and a dropping funnel and the acid is cooled to about 0° C. with a mixture of ice and salt. 0.8 mol (100 ml) of 2-nitroanisole is added drop by drop and the solution is then allowed to come back to room temperature; after a contact time of 30 minutes, the reaction mixture is poured onto one fifth of its volume of crushed ice. The sulphonyl chloride precipitates in the form of an oil; this is extracted with chloroform. After evaporation of the organic phase, the sulphonyl chloride is crystallized in a benzene/petroleum ether mixture.

Workup

  1. customequipped with a stirring system
  2. customto come back to room temperature
  3. additionafter a contact time of 30 minutes, the reaction mixture is poured onto one fifth of its volume of crushed ice
  4. customThe sulphonyl chloride precipitates in the form of an oil
  5. extractionthis is extracted with chloroform
  6. customAfter evaporation of the organic phase
  7. customthe sulphonyl chloride is crystallized in a benzene/petroleum ether mixture

Sources & evidence

ORD record
ord-7659d206a2674a9bbe3e9e286c1bbe38
Source dataset
uspto-grants-1980_07
Patent number
US04211776

Reaction notes

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