Sulfuric Acid → Bis(1-methylethyl) 2-chloro-1,4-benzenedicarboxylate

HRID 1381717Notes

Reaction equation

HRID 1381717 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].OS(O)(=O)=O>C(O)(C)C.OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH:2]([CH3:7])[CH3:3])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([O:13][CH:5]([CH3:6])[CH3:4])=[O:12]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 747852-Chloroterephthalic acid

Product 1

HCID 14372231Bis(1-methylethyl) 2-chloro-1,4-benzenedicarboxylate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

To 2.0 g of product from Example 1 suspended in 25 ml of isopropyl alcohol was added 0.3 ml of conc. H2SO4 and the reaction mixture heated at reflux for about 18 hours. Conc. H2SO4 (5 drops) was then added and heating continued for an additional 24 hours. The reaction mixture was cooled to room temperature. The solvent was removed and the residue treated with 50 ml of saturated sodium bicarbonate solution and 50 ml of ethyl acetate. The organic phase was dried over sodium sulfate and the solvent removed under nitrogen. Dissolution in pentane followed by removal of the solvent gave the above product.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for about 18 hours
  3. temperatureheating
  4. customThe solvent was removed
  5. additionthe residue treated with 50 ml of saturated sodium bicarbonate solution and 50 ml of ethyl acetate
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customthe solvent removed under nitrogen
  8. dissolutionDissolution in pentane
  9. customfollowed by removal of the solvent
  10. customgave the above product

Sources & evidence

ORD record
ord-baea4a33f56042d1beeb86ba3e79f8b5
Source dataset
uspto-grants-1989_02
Patent number
US04803294

Reaction notes

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