Ammonia → 4-(tert-Butylamino)benzoic acid

HRID 1416214Notes

Reaction equation

HRID 1416214 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N.[OH-].[K+].Cl>C(O)(C)(C)C.C(O)C.O>[C:5]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)([CH3:11])([CH3:6])[CH3:4]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 2337BenzocaineHCID 14797Potassium Hydroxide

Product 1

HCID 119590564-(tert-Butylamino)benzoic acidYield 24.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Ethyl 4-aminobenzoate (165 g) and 95% sulfuric acid (24.5 g) were refluxed in tert-butanol (560 ml) with stirring for 16 hours. The reaction mixture neutralized with 28% aqueous ammonia, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), thereby yielding an oil. The oil was dissolved in ethanol (100 ml) and then potassium hydroxide (23.5 g) and water (20 ml) were added thereto. The mixture was refluxed with stirring for 2 hours, neutralized the mixture 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 23.5 g of the aimed compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate anhydride
  3. concentrationconcentrated under a vacuum
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  5. customyielding an oil
  6. temperatureThe mixture was refluxed
  7. stirringwith stirring for 2 hours
  8. extractionextracted with ethyl acetate
  9. dry with materialThe extract was dried over sodium sulfate anhydride
  10. concentrationconcentrated under a vacuum
  11. customThe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-458c062da1264c509554eefae182b0a7
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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