Benzene, 1,3-bis(chloromethyl)- → HCID 19027424, compound

HRID 1081521Notes

Reaction equation

HRID 1081521 reaction equation
[C:1]1([CH2:9]Cl)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7]Cl)[CH:2]=1.[S:11]([O-:14])([O-:13])=[O:12].[Na+:15].[Na+]>C1(C)C=CC=CC=1.O>[C:1]1([CH2:9][S:11]([O-:14])(=[O:13])=[O:12])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][S:11]([O-:14])(=[O:13])=[O:12])[CH:2]=1.[Na+:15].[Na+:15]

Participants

5

Reactant 2

HCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 24437Sodium Sulfite

Product 1

HCID 19027424HCID 19027424, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a 300-ml egg-plant type flask provided with cooling pipe for reflux, 17.5 g (0.1 mol) of m-xylylene dichloride was dissolved in 40 ml of toluene, and a solution of 28.0 g (0.22 mol) of sodium sulfite in 40 ml of distilled water was put into the flask. The mixture in the flask was heated in an oil bath kept at 130° C. under refluxing for 24 h, while the mixture was vigorously stirred with a magnetic stirrer using teflon-coated stirring pieces. After that the reaction mixture was cooled to room temperature, and a white precipitate was collected by filtration. The precipitate was dried under reduced pressure and purified by well washing with diethyl ether and then recrystallizing in a 2:1 mixture of water and methanol. The purified product was 16.5 g of sodium m-xylylenedisulfonate (53% yield). The sodium salt was dissolved in distilled water and passed through a column of an ion-exchange resin (Duolite C-20 of Wako Junyaku Co.) to obtain the aimed disulfonic acid.

Workup

  1. customIn a 300-ml egg-plant type flask provided
  2. temperaturewith cooling pipe
  3. temperaturefor reflux
  4. temperatureThe mixture in the flask was heated in an oil bath
  5. customkept at 130° C.
  6. temperatureunder refluxing for 24 h, while the mixture
  7. stirringstirring pieces
  8. filtrationa white precipitate was collected by filtration
  9. customThe precipitate was dried under reduced pressure
  10. custompurified
  11. washby well washing with diethyl ether
  12. customrecrystallizing in a 2:1 mixture of water and methanol

Sources & evidence

ORD record
ord-b2f49672e0f14bf4a63369be0938aac9
Source dataset
uspto-grants-1996_12
Patent number
US05586001

Reaction notes

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