Chlorosulfonic acid → 2-Carboxymethoxy-4-chlorosulfonylphenoxyacetic acid

HRID 2182896Notes

Reaction equation

HRID 2182896 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11])([OH:3])=[O:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>>[C:10]([CH2:9][O:8][C:7]1[CH:13]=[C:14]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:15]=[CH:16][C:6]=1[O:5][CH2:4][C:1]([OH:3])=[O:2])([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 794272,2'-(1,2-Phenylenebis(oxy))bisacetic acid

Product 1

HCID 207863452-Carboxymethoxy-4-chlorosulfonylphenoxyacetic acid

Procedure

2-Carboxymethoxyphenoxyacetic acid (15.3 g, 0.0675 mol) was added in portions over 30 min to stirred chlorosulfonic acid (59.0 g, 0.506 mol) that was cooled in an ice/methanol bath. The mixture was allowed to warm to room temperature over 2.5 hr and was then poured slowly into stirred ice water. The resulting solid was collected by filtration, washed with water, and dried at high vacuum over sodium hydroxide. The product, title compound, weighed 6.54 g (30%).

Workup

  1. temperaturewas cooled in an ice/methanol bath
  2. additionwas then poured slowly
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. dry with materialdried at high vacuum over sodium hydroxide

Sources & evidence

ORD record
ord-4c81b6e6bec440e88ebad9e98c5cc1c1
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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