Chlorosulfonic acid → Ethyl {[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}acetate

HRID 1746411Notes

Reaction equation

HRID 1746411 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[CH3:14])[CH3:2].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[Cl:16][S:17]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[C:8]([CH3:14])[C:9]=1[CH3:13])(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 17065225Ethyl [(2,3-dimethylphenyl)oxy]acetate

Product 1

HCID 19261654Ethyl {[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}acetate

Procedure

Ethyl[(2,3-dimethylphenyl)oxy]acetate (6.1 g, 29.3 mmol) was added dropwise to chlorosulfonic acid (8.78 mL, 132 mmol) at 0° C., with stirring, causing a blood red solution. Reaction stirred for 30 minutes, then allowed to warm to RT. Mixture was stirred for a further 2 hours, then quenched by pouring over ice/water (200 mL). A dark red gum formed, this was extracted into dichloromethane (3×100 mL). Organics were concentrated in vacuo, to give a thick red oil, which crystallized on standing. Product was dried overnight in vacuum oven, to yield 8.179 g as red crystals. No further purification carried out. RT 1.25 mins.

Workup

  1. customReaction
  2. stirringstirred for 30 minutes
  3. stirringMixture was stirred for a further 2 hours
  4. customquenched
  5. additionby pouring over ice/water (200 mL)
  6. customA dark red gum formed
  7. extractionthis was extracted into dichloromethane (3×100 mL)
  8. concentrationOrganics were concentrated in vacuo
  9. customto give a thick red oil, which
  10. customcrystallized
  11. customProduct was dried overnight in vacuum oven
  12. customto yield 8.179 g as red crystals
  13. customNo further purification
  14. customRT 1.25 mins

Sources & evidence

ORD record
ord-d86ee55bf0e746bba25d24bfaf7d3d25
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

Loading…