Chlorosulfonic acid → 2-Tosylethyl 2-(4-(chlorosulfonyl)phenoxy)acetate

HRID 2182842Notes

Reaction equation

HRID 2182842 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:24][S:25](O)(=[O:27])=[O:26]>C(Cl)Cl>[C:1]1([CH3:23])[CH:2]=[CH:3][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([S:25]([Cl:24])(=[O:27])=[O:26])=[CH:20][CH:21]=2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 695571462-(4-Methylbenzene-1-sulfonyl)ethyl phenoxyacetate2×

Product 1

HCID 593166882-Tosylethyl 2-(4-(chlorosulfonyl)phenoxy)acetateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-bath cooled mixture of phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 3, 3.0 g) and 1 mL of CH2Cl2 was added drop-wise 3.0 mL of chlorosulfonic acid (5.2 g, 5.0 eq). After the addition of the chlorosulfonic acid was complete the ice bath was removed. The mixture was continued to stir at room temperature for 3 h. Thereafter the thick syrupy mixture was poured onto the crushed ice with vigorous stirring. White precipitates were collected by filtration, were washed with methanol and cold benzene, and dried overnight under high vacuum to yield 3.4 g (87%) of Intermediate 4 as white powder.

Workup

  1. temperatureTo an ice-bath cooled
  2. customwas removed
  3. additionThereafter the thick syrupy mixture was poured onto the crushed ice with vigorous stirring
  4. customWhite precipitates
  5. filtrationwere collected by filtration
  6. washwere washed with methanol and cold benzene
  7. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-69576d7c4d934fb498bac7808876e5cd
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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