Dichloromethane → HCID 22479312, compound

HRID 2182895Notes

Reaction equation

HRID 2182895 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1C.[Cl:18][S:19]([OH:22])(=O)=[O:20].Cl[CH2:24]Cl>>[Cl:18][S:19]([C:7]1[C:6]([CH3:24])=[CH:5][C:4]([O:9][CH2:10][C:11]([CH3:16])([CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[CH3:1])(=[O:22])=[O:20]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 22479338HCID 22479338, compound2×

Product 1

HCID 22479312HCID 22479312, compoundYield 29%

Conditions

Temperature
-2 °C

Procedure

Methyl 3-(3,4-dimethylphenyloxy)-2,2-dimethylpropionate (Intermediate A8, 23.6 g, 0.100 mol) was added dropwise over 30 min to rapidly stirred chlorosulfonic acid (46.6 g, 0.400 mol) while the reaction temperature was maintained at −2° C. The reaction mixture was then poured into a stirred mixture of 300 g ice and 300 mL of dichloromethane. The aqueous phase was extracted with additional dichloromethane, and the combined organic layers were washed with water, 0.5 M sodium bicarbonate (×2), and water. The solvent was removed at aspirator pressure and the residue was purified by several passes of flash chromatography (silica gel: hexanes→2% ethyl acetate in hexanes) to yield 9.6 g (29%) of the title compound.

Workup

  1. extractionThe aqueous phase was extracted with additional dichloromethane
  2. washthe combined organic layers were washed with water, 0.5 M sodium bicarbonate (×2), and water
  3. customThe solvent was removed at aspirator pressure
  4. customthe residue was purified by several passes of flash chromatography (silica gel: hexanes→2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-79b01f2bc2e64453a7360553107c12af
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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