Chlorosulfonic acid → 2-Carboxymethoxy-4-chlorosulfonylphenoxyacetic acid

HRID 1593236Notes

Reaction equation

HRID 1593236 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-0764c354857f4a9daf93c15dffc7f463
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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