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

HRID 637521Notes

Reaction equation

HRID 637521 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].O=S(Cl)Cl>>[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

4

Reactant 3

HCID 84492,4-DichlorophenolHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideYield 94%

Conditions

Temperature
25 °C

Procedure

Molten 2,4-dichlorophenol (82.7 g) was contacted with 166 ml of chlorosulfonic acid at 37°-40° C. over a 1 hour period. After a 15 minute hold at 40° C. the reaction was cooled to 25° C. and 73 ml of SOCl2 was added. The temperature was raised to 32° C. for 40 minutes and then allowed to cool to 25° C. over 1 hour. The reaction mixture was quenched onto ice. Filtration and drying afforded 126.7 g of 99% pure 2-hydroxy-3,5-dichlorobenzenesulfonyl chloride (C) (94% yield).

Workup

  1. temperatureThe temperature was raised to 32° C. for 40 minutes
  2. temperatureto cool to 25° C. over 1 hour
  3. customThe reaction mixture was quenched onto ice
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-e90a9ca5912346bdab1768ca8936e1ab
Source dataset
uspto-grants-1985_12
Patent number
US04556733

Reaction notes

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