Dimethyl Carbonate → Methylene bis(4-methoxybenzenesulfonate)

HRID 1021006Notes

Reaction equation

HRID 1021006 reaction equation
[S:1](Cl)([O:4][CH2:5][O:6][S:7](Cl)(=[O:9])=[O:8])(=[O:3])=[O:2].[NH+]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](S([O-])(=O)=O)=[CH:22][CH:21]=1.[C:30](=O)(OC)[O:31][CH3:32]>>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:1]([O:4][CH2:5][O:6][S:7]([C:15]2[CH:16]=[CH:17][C:30]([O:31][CH3:32])=[CH:13][CH:14]=2)(=[O:9])=[O:8])(=[O:3])=[O:2])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 9837734Methylene bis(chlorosulfate)HCID 89599766HCID 89599766, compound

Product 1

HCID 86665804Methylene bis(4-methoxybenzenesulfonate)

Procedure

In dimethyl carbonate (30 mL), methylene bis(chlorosulfate) [CISO2OCH2OSO2Cl] (4.5 g, 13 mmol) was reacted with 4-methoxybenzenesulfonic acid pyridinium salt (7 g, 26 mmol) under agitation at 55° C. for 2 hours. After the reaction was completed, precipitated chlorosulfonic acid pyridinium salt was separated through filtration. Washing with water was performed and, subsequently, concentration was performed under reduced pressure, so as to obtain a pale red transparent oil. Refining was performed through recrystallization, so as to obtain a desired product, methylene bis(4-methoxybenzenesulfonate), at a yield of 32% (1.65 g, 4.2 mmol). The measurement result of 1H NMR is as described below.

Workup

  1. customprecipitated chlorosulfonic acid pyridinium salt
  2. customwas separated through filtration
  3. washWashing with water
  4. concentrationsubsequently, concentration
  5. customso as to obtain a pale red transparent oil
  6. customRefining was performed through recrystallization

Sources & evidence

ORD record
ord-d4701e1f41334bc4b486c049b3469ab2
Source dataset
uspto-grants-2014_05
Patent number
US08716513B2

Reaction notes

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