Naphthalene → 1,5-Naphthalenedisulfonyl chloride

HRID 846308Notes

Reaction equation

HRID 846308 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:11][S:12]([OH:15])(=O)=[O:13]>S(=O)(=O)(O)N>[C:9]1([S:12]([Cl:11])(=[O:15])=[O:13])[C:10]2[CH:1]=[CH:2][CH:3]=[C:4]([S:12]([Cl:11])(=[O:15])=[O:13])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 931NaphthaleneHCID 24638Chlorosulfonic acid

Product 1

HCID 159941,5-Naphthalenedisulfonyl chlorideYield 105.8%

Reagents, catalysts & solvents 1

HCID 5987Sulfamic AcidCatalyst

Procedure

64.1 g (0.5 mol) of naphthalene are introduced with ice cooling into 640.7 g (5.5 mol) of chlorosulfonic acid, to which 1 g of sulfamic acid has been added. The mixture is then stirred at room temperature for 4 hours. The reaction mixture is added dropwise to ice water, and the precipitated crystals are filtered off with suction and washed with water. 172.1 g of naphthalene-1,5-disulfonyl chloride having a water content of 26.5% and a chloride content of 71.6%, corresponding to 123.2 g (75.7%), are obtained.

Workup

  1. additionhas been added
  2. filtrationthe precipitated crystals are filtered off with suction
  3. washwashed with water

Sources & evidence

ORD record
ord-5d9872eb67434e349bc32ea661007932
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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