Methyl Chloride → HCID 54071738, compound

HRID 2379029Notes

Reaction equation

HRID 2379029 reaction equation
Cl[CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([Cl:10])[C:6]([CH2:11]Cl)=[C:5]([Cl:13])[C:4]=1[Cl:14].C[O:16][P:17]([O:20][CH3:21])[O:18][CH3:19].CCl>C1(C)C=CC=CC=1>[CH3:19][O:18][P:17]([CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([Cl:10])[C:6]([CH2:11][P:17](=[O:16])([O:20][CH3:21])[O:18][CH3:19])=[C:5]([Cl:13])[C:4]=1[Cl:14])(=[O:16])[O:20][CH3:21]

Participants

5

Reactant 3

HCID 6327Methyl ChlorideHCID 8472Trimethyl phosphiteHCID 66179Alpha,alpha',2,3,5,6-hexachloro-4-xylene

Product 1

HCID 54071738HCID 54071738, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of α,α',2,3,5,6-hexachloro-p-xylene (6.26 g, 0.02 mol) in toluene (60 mL) and trimethylphosphite (7.0 mL, 7.4 g, 0.06 mol) is heated to reflux temperature. The flask is set up with a condenser, Dean-Stark trap, and the nitrogen inlet positioned so that any methyl chloride produced in the reaction will be swept out the condenser. A clear solution resultes with heating and the solution is heated at reflux for 18 hours. The toluene is distilled from the flask via the Dean-Stark trap, more trimethylphosphite is added (7.0 mL), and the reaction is heated with an oil bath (~110° C.) for 48 hours. After standing at room temperature, a white solid formed in the flask. A TLC indicated that no starting material remained. Toluene (100 mL) is added to flask and the mixture is heated at reflux temperature with stirring until a clear solution is obtained. The reaction mixture is allowed to cool to room temperature and a white precipitate formed. The white solid is collected by filtration, washed with hexane, dried in a vacuum desiccator, to give 5.17 g of title compound, mp 179°-181° C. Recrystallization from ethyl acetate gives 2.44 g as white crystals, mp 181°-182° C. There are some problems keeping the product in solution during the filtration of the hot ethyl acetate solution so that a considerable amount of material crystallized out during filtration. These crystals are combined with the filtrate from the collection of the first crop and yielded. 2.27 g. This material is recrystallized from ethyl acetate giving a second crop of 2.22 g, mp 181°-182° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. customThe flask is set up with a condenser
  4. customproduced in the reaction
  5. customA clear solution resultes
  6. temperaturewith heating
  7. temperaturethe solution is heated
  8. temperatureat reflux for 18 hours
  9. distillationThe toluene is distilled from the flask via the Dean-Stark trap, more trimethylphosphite
  10. additionis added (7.0 mL)
  11. temperaturethe reaction is heated with an oil bath (~110° C.) for 48 hours
  12. customAfter standing at room temperature
  13. customa white solid formed in the flask
  14. temperaturethe mixture is heated
  15. temperatureat reflux temperature
  16. customis obtained
  17. customa white precipitate formed
  18. filtrationThe white solid is collected by filtration
  19. washwashed with hexane
  20. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-1ae15899c2154e8884afe11cd11d445c
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Reaction notes

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