Chlorosulfonic acid → 2-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride

HRID 908167Notes

Reaction equation

HRID 908167 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:11][C:12]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 796991-(p-Chlorophenyl)acetone

Product 1

HCID 578311052-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride

Procedure

To chlorosulfonic acid (25 ml, excess) cooled at −10° C. is added dropwise 4-chlorophenyl acetone (1.0 g, 5.93 mmol). The temperature is kept below 0° C. throughout the addition. The reaction mixture is then left to warm up to room temperature overnight. The reaction mixture is poured carefully onto ice (1500 ml). Once the ice is melted, the aqueous layer is extracted with dichloromethane (3×250 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford the titled compound as an off-white solid.

Workup

  1. additionThe temperature is kept below 0° C. throughout the addition
  2. waitThe reaction mixture is then left
  3. additionThe reaction mixture is poured carefully onto ice (1500 ml)
  4. extractionthe aqueous layer is extracted with dichloromethane (3×250 ml)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-46af83de1ccc4d039a7d8b18a39b825f
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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