Dichloromethane → 2,5-Dimethoxybenzenesulfonyl chloride

HRID 479267Notes

Reaction equation

HRID 479267 reaction equation
C(Cl)Cl.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[Cl:14][S:15](O)(=[O:17])=[O:16].P(Cl)(Cl)(Cl)=O>CN(C)C(=O)C.C(#N)C>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[S:15]([Cl:14])(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 90161,4-DimethoxybenzeneHCID 24638Chlorosulfonic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 1370252,5-Dimethoxybenzenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
35 °C

Procedure

Into 1100 ml of methylene chloride was dissolved 552 g (4.00 mol) of commercially available 1,4-dimethoxybenzene, and then 308 ml (4.63 mol) of chlorosulfonic acid was added dropwise thereto under cooling with ice in such a manner that the internal temperature was not over 5° C. After the addition, the reaction system was put under a condition of room temperature, and the solution was further stirred for 1 hour. Next, 1000 ml of acetonitrile and 600 ml of DMAC (N,N-dimethylacetoamide) were poured into the solution. Next, the reaction system was heated in a warm bath of 35° C. temperature, and thereto was added dropwise 404 ml (4.33 mol) of phosphorous oxychloride at an internal temperature of 30° C. At this time, attention was paid that the internal temperature was not over 40° C. After the addition, the solution was allowed to react at 35° C. for 1 hour. Thereafter, the reaction solution was charged into ice water. The organic phase was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure, to obtain 2,5-dimethoxybenzenesulfonylchloride.

Workup

  1. temperatureunder cooling with ice in such a manner that the internal temperature
  2. customwas not over 5° C
  3. additionAfter the addition
  4. customwas put under a condition of room temperature
  5. customwas not over 40° C
  6. additionAfter the addition
  7. customto react at 35° C. for 1 hour
  8. extractionThe organic phase was extracted with ethyl acetate
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-a3e3d84887344fa7b605bdc5875bf68d
Source dataset
uspto-grants-2003_11
Patent number
US06645711B2

Reaction notes

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