Dichloromethane → Methyl 3-(4-chlorosulfonylphenoxy)-2,2-dimethylpropanoate

HRID 1593245Notes

Reaction equation

HRID 1593245 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[Cl:16][S:17](O)(=[O:19])=[O:18].ClCCl>CO>[Cl:16][S:17]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:2]([CH3:15])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[CH:14][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 22479306Methyl 2,2-dimethyl-3-phenoxypropanoate

Product 1

HCID 20786564Methyl 3-(4-chlorosulfonylphenoxy)-2,2-dimethylpropanoateYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

Methyl 2,2-dimethyl-3-phenoxypropionate (Intermediate A36, 36 g, 0.17 mol) was added dropwise over 60 min to rapidly stirred chlorosulfonic acid that was maintained at −5° C. The mixture was warmed to room temperature, stirred for an additional 90 min, and poured into a cooled, rapidly stirring mixture of dichloromethane (250 mL) and methanol (30 mL). The mixture was stirred for 30 min while being cooled and then for 60 min at room temperature. It was then washed with several portions of ice-water. The combined aqueous layers were extracted with a small portion of dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was stirred with hexanes and collected by filtration to yield 19 g (36%) of the title compound, sulfonyl chloride.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. additionpoured into a cooled
  3. stirringrapidly stirring
  4. stirringThe mixture was stirred for 30 min
  5. temperaturewhile being cooled
  6. waitfor 60 min at room temperature
  7. washIt was then washed with several portions of ice-water
  8. extractionThe combined aqueous layers were extracted with a small portion of dichloromethane
  9. washThe combined organic layers were washed with saturated aqueous sodium chloride
  10. dry with materialdried over sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. stirringthe residue was stirred with hexanes
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e6083731d2314d9ebcc00655f4fb4a99
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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