Practicals Semester IV Syllabus Syllabus Benzocaine
• Local anesthetic agent
• Indicated to treat a variety of pain-related conditions. It may be used for: • Local anesthesia of oral and pharyngeal mucous membranes (sore throat, cold sores, mouth ulcers, toothache, sore gums, denture irritation) • Otic pain (earache) • Surgical or procedural local anesthesia • Functional groups • Ester • Aromatic amine Synthesis • Benzocaine can be synthesized from Para Amino Benzoic Acid (PABA) and ethanol
• The interaction between a carboxylic acid and an alcohol is a reversible process
and proceeds very slowly. Equilibrium is only attained after refluxing for several days. Synthesis • Benzocaine can be synthesized from Para Amino Benzoic Acid (PABA) and ethanol
• If about 3% of either conc. sulphuric acid or a dry hydrogen chloride is added to a
mixture, the same point of equilibrium can be reached after few hours. Rate of forward reaction is enhanced • Rate of forward reaction is enhanced by - • The equilibrium may be displaced towards the right by using sulphuric acid as a catalyst. • The equilibrium may be displaced towards formation of the ester by the use of excess of any of the reactants. It is frequently convenient to use an excess of the acid, but if the acid is expensive a large excess of alcohol can be employed. Mechanism NH3+
Sod carbonate
• Since sulfuric acid is used to catalyse the esterification, the
benzocaine formed exists as sulphate salt. • To release free ethyl-4-amino benzoate, an alkali like sodium carbonate is added. • Excess of sodium carbonate if added can cause a base catalyzed hydrolysis of ester. So it should be added just to make the pH neutral. • Use of strong bases like NaOH should be avoided as they may hydrolyse the ester formed. Procedure Mole table Theoretical yield
Stoichiometric ratio 1 mole PABA gives 1 mole Benzocaine
Physical Organic Chemistry—Ii: Specially Invited Lectures Presented at the Second IUPAC Conference on Physical Organic Chemistry Held at Noordwijkerhout, Netherlands, 29 April–2 May 1974