2,4-Dichlorophenol → 3,5-Dichloro-2-hydroxybenzenesulphonyl chloride

HRID 637519Notes

Reaction equation

HRID 637519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>>[OH:9][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[S:11]([Cl:10])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 84492,4-DichlorophenolHCID 24638Chlorosulfonic acid

Product 1

HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideYield 77%

Conditions

Temperature
24 °C

Procedure

Molten 2,4-dichlorophenol (82.13 g) was added to 166 ml of ClSO3H at 37°-40° C. over a 1 hour period. After a 20 minute hold period at 37°-40° C. the mixture was cooled to 24° C. and held an additional 1 hour. The reaction mixture was then cautiously poured onto 1100 g of ice with constant agitation. Filtration, washing and drying afforded 104 g of 97.6% pure 2-hydroxy-3,5-dichlorobenzenesulfonyl chloride (C) (77% yield), mp 79°-82° C.

Workup

  1. waitheld an additional 1 hour
  2. filtrationFiltration
  3. washwashing
  4. customdrying

Sources & evidence

ORD record
ord-2f9d3163f3804f479dad761480e60c66
Source dataset
uspto-grants-1985_12
Patent number
US04556733

Reaction notes

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