Chlorosulfonic acid → 2-{[4-(Chlorosulfonyl)phenyl]oxy}ethyl 2-propenoate

HRID 1487032Notes

Reaction equation

HRID 1487032 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])[CH:2]=[CH2:3].[Cl:15][S:16](O)(=[O:18])=[O:17]>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O>[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:13][CH:14]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 24638Chlorosulfonic acidHCID 39485Phenoxyethyl acrylate

Product 1

HCID 898762902-{[4-(Chlorosulfonyl)phenyl]oxy}ethyl 2-propenoate

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-(phenyloxy)ethyl 2-propenoate (5 g, 26.0 mmol) in dichloromethane (50 mL), was cooled to 0° C. Chlorosulfonic acid (5.21 mL, 78 mmol) was added dropwise over 15 minutes at 0° C. then the mixture was allowed to warm to room temperate over 30 minutes. The reaction mixture was stirred overnight (16 hours) at room temperature. The solution was then poured onto ice and extracted with dichloromethane (3×50 mL). Resulting emulsion was diluted with ethyl acetate (200 mL) and brine (50 mL) in order to achieve separation of phases. The aqueous layer was further extracted with ethyl acetate (100 mL). The combined organic fractions were dried with magnesium sulphate then evaporated in vacuo to give an oily solid, which was dried under high vacuum overnight. After drying, a sticky solid was isolated (3.2 g) and this was taken on to the next step without further purification. LCMS [LCMS1] Rt 0.47 min, m/z (ES−) 272 (M−Cl+OH).

Workup

  1. temperatureto warm to room temperate over 30 minutes
  2. additionThe solution was then poured onto ice
  3. extractionextracted with dichloromethane (3×50 mL)
  4. customResulting emulsion
  5. customseparation of phases
  6. extractionThe aqueous layer was further extracted with ethyl acetate (100 mL)
  7. dry with materialThe combined organic fractions were dried with magnesium sulphate
  8. customthen evaporated in vacuo
  9. customto give an oily solid, which
  10. customwas dried under high vacuum overnight
  11. customAfter drying
  12. customa sticky solid was isolated (3.2 g)
  13. customthis was taken on to the next step without further purification

Sources & evidence

ORD record
ord-35ac55e395b84b6eb0c2bc3508c342e8
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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