Hydrochloric Acid → 2,3,5,6-Tetramethylbenzene-1,4-dicarbonyl dichloride

HRID 437327Notes

Reaction equation

HRID 437327 reaction equation
[CH3:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([CH3:11])[C:5]([CH3:12])=[C:4]([C:13](O)=[O:14])[C:3]=1[CH3:16].S(Cl)([Cl:19])=O.S(=O)=O.[ClH:24]>>[CH3:1][C:2]1[C:7]([C:8]([Cl:24])=[O:9])=[C:6]([CH3:11])[C:5]([CH3:12])=[C:4]([C:13]([Cl:19])=[O:14])[C:3]=1[CH3:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24386Thionyl ChlorideHCID 2615432,3,5,6-Tetramethyl-1,4-benzenedicarboxylic acid

Product 1

HCID 202514342,3,5,6-Tetramethylbenzene-1,4-dicarbonyl dichloride

Procedure

To a 500 ml. three-necked flask equipped with stirrer, reflux condenser and nitrogen inlet is added 100 grams tetramethylterephthalic acid and 200 ml. thionyl chloride. The mixture is stirred at reflux of 6 hours during which time the acid dissolves and a mixture of sulfur dioxide and hydrogen chloride is evolved. At the end of this period the excess thionyl chloride is removed by distillation. The crude tetramethylterephthaloyl chloride is recrystallized twice from cyclohexane.

Workup

  1. customthree-necked flask equipped with stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureat reflux of 6 hours during which time the acid
  4. dissolutiondissolves
  5. customAt the end of this period the excess thionyl chloride is removed by distillation
  6. customThe crude tetramethylterephthaloyl chloride is recrystallized twice from cyclohexane

Sources & evidence

ORD record
ord-2df5495a9d7449b5ba1e92140563b0d8
Source dataset
uspto-grants-1977_06
Patent number
US04031063

Reaction notes

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