Chlorosulfonic acid → 5-(Chlorosulfonyl)-2-ethoxybenzoic acid

HRID 1061562Notes

Reaction equation

HRID 1061562 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Cl:13][S:14]([C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7])(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 672522-Ethoxybenzoic acid

Product 1

HCID 113800715-(Chlorosulfonyl)-2-ethoxybenzoic acidYield 81.1%

Procedure

In a 250 ml three-neck flack, 2-ethoxy benzoic acid (50 g, 0.30 mol) was added dropwise to an ice-cooled mixtures of sulfoxide dichloride (22 ml, 0.30 mol) and chlorosulfonic acid (82.6 ml, 1.24 mol) under stirring. At the same time, the temperature of the reacting mixture was kept below 25° C. The resulting mixture was stirred at room temperature for 18 hours and then poured into ice water with stirring, and white deposit appeared. The reaction mixture was stirred for another 1 hour, filtered, washed with water, and dried in vacuum, which gave 64.4 g of crude product as white solid (II) (yield 81%). m.p. 108-110° C. The crude product was used directly in the next step without further purification.

Workup

  1. customwas kept below 25° C
  2. stirringThe resulting mixture was stirred at room temperature for 18 hours
  3. stirringwith stirring
  4. stirringThe reaction mixture was stirred for another 1 hour
  5. filtrationfiltered
  6. washwashed with water
  7. customdried in vacuum, which

Sources & evidence

ORD record
ord-8ee70eb9e8284c9bb991c6a0a8a541e4
Source dataset
uspto-grants-2005_11
Patent number
US06960592B2

Reaction notes

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