Iodine → HCID 21330831, compound

HRID 1391279Notes

Reaction equation

HRID 1391279 reaction equation
ClC1C(C)=C(Cl)C(Cl)=C(C)C=1Cl.[Cl:13][C:14]1[C:19]([Cl:20])=[C:18]([CH2:21][OH:22])[C:17]([Cl:23])=[C:16]([Cl:24])[C:15]=1[CH2:25]O.S(=O)=O.II>>[Cl:13][C:14]1[C:19]([Cl:20])=[C:18]([CH:21]=[O:22])[C:17]([Cl:23])=[C:16]([Cl:24])[C:15]=1[CH3:25]

Participants

5

Reactant 4

HCID 807IodineHCID 1119Sulfur DioxideHCID 134112,3,5,6-Tetrachloro-p-xyleneHCID 815902,3,5,6-Tetrachloro-1,4-benzenedimethanol

Product 1

HCID 21330831HCID 21330831, compound

Procedure

When the procedure of Example 64 was carried by replacing tetrachloro-p-xylene with an equimolar amount (27.6g) of 2,3,5,6-tetrachloro-p-xylene-α,α'-diol, a strong evolution of sulfur dioxide was observed (identified qualitatively by iodine paper), but the resultant solution did not turn purple, instead it acquired a brown amber color. After a four hour of heating period between 90 and 94° C., the clear solution was poured, after it cooled to room temperature, onto ice, yielding a yellow slurry. Since filtration was sluggish, the slurry was extracted with diethyl ether, yielding, after evaporation of the solvent 19.0 g of bright yellow solids, whose identity was determined by infrared and nuclear magnetic resonance spectra, which matched those described in Example 64.

Workup

  1. temperatureAfter a four hour of heating period between 90 and 94° C.
  2. additionthe clear solution was poured
  3. customyielding a yellow slurry
  4. filtrationSince filtration
  5. extractionthe slurry was extracted with diethyl ether
  6. customyielding
  7. customafter evaporation of the solvent 19.0 g of bright yellow solids, whose identity

Sources & evidence

ORD record
ord-af8670edace44f1f82028909481bbd97
Source dataset
uspto-grants-1979_02
Patent number
US04141912

Reaction notes

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