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

HRID 258970Notes

Reaction equation

HRID 258970 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 for six 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 residue, which is 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 for six hours during which time the acid
  4. dissolutiondissolves
  5. customAt the end of this period the excess thionyl chloride is removed by distillation
  6. customis recrystallized twice from cyclohexane

Sources & evidence

ORD record
ord-9a963eb1ab7f4e209eb4a65dc8cdc5da
Source dataset
uspto-grants-1977_07
Patent number
US04035437

Reaction notes

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