Chlorosulfonic acid → 2-(4-Tolylsulfonyl)ethyl 4-chlorosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate

HRID 2182870Notes

Reaction equation

HRID 2182870 reaction equation
[C:1]1([CH3:40])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:39])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][C:24]([O:26][CH2:27][CH2:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[O:25])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:41][S:42](O)(=[O:44])=[O:43]>ClCCl>[C:35]1([CH3:38])[CH:36]=[CH:37][C:32]([S:29]([CH2:28][CH2:27][O:26][C:24](=[O:25])[CH2:23][O:22][C:17]2[CH:18]=[CH:19][C:20]([S:42]([Cl:41])(=[O:44])=[O:43])=[CH:21][C:16]=2[O:15][CH2:14][C:13]([O:12][CH2:11][CH2:10][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:40])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[O:39])(=[O:30])=[O:31])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 20786414{2-[2-(Toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl ester2×

Product 1

HCID 224793092-(4-Tolylsulfonyl)ethyl 4-chlorosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

{2-[2-(Toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 37) (13 g, 22 mmole) was added to dichloromethane (30 mL), and cooled in an ice bath. Chlorosulfonic acid (10 mL) was slowly added, and the mixture was stirred at 0° C. for 2 hr., then at room temperature for 1 hr. Thereafter it was poured into crushed ice (200 g) with stirring. The precipitates were extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated, the residue was dried in vacuo to yield 17.3 g of {4-chlorosulfonyl-2-[2-(toluene-4-sulfonyl)-ethoxycarbonylmethoxy]-phenoxy}-acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 38).

Workup

  1. temperaturecooled in an ice bath
  2. wait, then at room temperature for 1 hr
  3. additionThereafter it was poured
  4. stirringwith stirring
  5. extractionThe precipitates were extracted with dichloromethane
  6. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-6480389ebf2842279a9f2edef6eae620
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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