Sulfuric Acid → 4-tert-Butoxybenzoic Acid

HRID 1416213Notes

Reaction equation

HRID 1416213 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH2:13]=[C:14]([CH3:16])[CH3:15].S(=O)(=O)(O)O>ClCCl>[C:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 8434Ethylparaben

Product 1

HCID 5353024-tert-Butoxybenzoic AcidYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-hydroxybenzoate (16.6 g), isobutene (25 g), and 95% sulfuric acid (0.5 ml) were stirred in dichloromethane (300 ml) overnight at 0° C. The reaction mixture was washed with 20% sodium carbonate aqueous solution, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was dissolved in ethanol (32 ml) and the solution, with potassium hydroxide (7.5 g) and water (6 ml) added thereto, was refluxed with stirring for 2 hours. The reaction mixture was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from ethyl acetate to yield 9.3 g of the aimed compound.

Workup

  1. washThe reaction mixture was washed with 20% sodium carbonate aqueous solution
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated under a vacuum
  4. dissolutionThe residue was dissolved in ethanol (32 ml)
  5. additionthe solution, with potassium hydroxide (7.5 g) and water (6 ml) added
  6. temperaturewas refluxed
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried over sodium sulfate anhydride
  9. concentrationconcentrated under a vacuum
  10. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-375162094a9b4d5fbfa2a4569e71bd62
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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