Hydrochloric Acid → HCID 13115422, compound

HRID 1165104Notes

Reaction equation

HRID 1165104 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)(Cl)C(Cl)Cl.[N+](C)([O-])=O.[C:15]([OH:26])(=[O:25])[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.S(=O)(=O)(O)O>>[OH:33][C:27]1[CH:32]=[CH:31][C:30]([C:20]([C:19]2[CH:18]=[CH:17][C:16]([C:15]([OH:26])=[O:25])=[CH:24][CH:23]=2)=[O:22])=[CH:29][CH:28]=1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 996PhenolHCID 1118Sulfuric AcidHCID 6375NitromethaneHCID 65911,1,2,2-TetrachloroethaneHCID 7489Terephthalic AcidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13115422HCID 13115422, compoundYield 50%

Conditions

Temperature
30 °C

Procedure

To a mixture formed by adding 0.4 moles of AlCl3 to 0.6 mole of sym-tetrachloroethane are sequentially added, with stirring, 0.46 mole of nitromethane, 0.2 mole of terephthalic acid (reagent grade) and gradually 0.2 mole of phenol. The initial temperature of the resulting mixture is 25° C. and the temperature is raised to about 30° C. after 2 hours, then to about 40° C. after 4 hours, and about 1 hour later or until all HCl evolution is complete, the resulting mixture is allowed to stand overnight at room temperature. The mixture is treated with dilute sulfuric acid and the sym-tetrachloroethane is distilled from the mixture. The recovered solid is redissolved in boiling 10% Na2CO3, filtered, reprecipitated with concentrated HCl, and finally washed with water. About a 50% yield of 4-(4-hydroxybenzoyl) benzoic acid of good purity is obtained.

Workup

  1. customTo a mixture formed
  2. additionare sequentially added
  3. customis 25° C.
  4. customabout 1 hour
  5. waitto stand overnight at room temperature
  6. distillationthe sym-tetrachloroethane is distilled from the mixture
  7. dissolutionThe recovered solid is redissolved
  8. filtrationfiltered
  9. customreprecipitated with concentrated HCl
  10. washfinally washed with water

Sources & evidence

ORD record
ord-5d3f76b5ae884fa98c53516ff08dfe3e
Source dataset
uspto-grants-1990_03
Patent number
US04906784

Reaction notes

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