Benzocaine is the derivative of p-aminobenzoic acid and can be synthesized via the Fischer esterification reaction. It can be prepared from p -toluidine by a four-step synthesis. The problem of a synthesis of this type is that the overall yield of the final product is usually quite low. 8.19.3 Procedure
How do you make benzocaine from ethyl esters?
The classic, optimal way of benzocaine synthesis is the reduction of the nitro group of the ethyl ester of 4-nitrobenzoic acid to benzocaine by hydrogen, which generates directly in the reaction medium by the reaction of iron filings with dilute acids [24–26 ]. Sign in to download full-size image
What is ferrofluid made of?
A ferrofluid is a liquid made of nanoscale ferromagnetic particles dispersed evenly throughout a carrier fluid. Ferrofluids become very strongly magnetized in the presence of a magnetic field. Here, Fe3O4 magnetite nanoparticles are produced by mixing Fe (II) and Fe (III) salts together in a basic solution.
How do you dissolve benzocaine?
Weigh approximately 150-170 mg of benzocaine into a 250 mL conical flask. Transfer 100 mL of acetic acid into the flask, and dissolve the benzocaine in the acid by placing the container in an ultrasonic bath at 20-25°C for 2-3 minutes. Add 10 mL of a mercuric acetate solution, and let the flask stand for 45 minutes.
What is the mechanism of action of benzocaine?
Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Benzocaine binds to the sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited,…
Is benzocaine protonated or ionic?
Benzocaine displayed two major IM peaks as a protonated ion, attributed to protonation at the N and O positions rather than separate conformers. Benzocaine is the ethyl ester of 4-aminobenzoic acid (2.3.1).
Synthesis of benzocaine: Into a 100 ml flask, mix 1.25 g of p-aminobenzoic acid hydrochloride, 10 ml of EtOH, and 0.5 ml H2SO4 (conc.). Heat the mixture at reflux for 2 h. After cooling the mixture, neutralize with an aqueous sodium carbonate solution (10%).
How is benzocaine synthesized industrially from P nitrobenzoic acid?
Benzocaine can be prepared by esterification using 4-aminobenzoic acid and ethanol. It can also be prepared by reduction of ethyl 4-nitrobenzoate to the amine. In industrial practice, the reducing agent is usually iron and water in the presence of a little acid.
How do you synthesis benzocaine?
A three-step synthesis is used to create benzocaine. First p- aminobenzoic acid is produced from taking p-acetotoluidide and oxidizing it with magnesium sulfate. Then to create an amino acid, p-aminobenzoic acid is then heated with hydrochloric acid.
What is the role of h2so4 in ethyl p aminobenzoate benzocaine from p-aminobenzoic acid?
The reaction mixture should dissolve completely in the water, since the ethyl p-aminobenzoate is in the form of the hydrogen salt. At this point the sulfuric acid is completely neutralized, and the ethyl p-aminobenzoate precipitates.
What is the molecular formula of benzocaine?
C9H11NO2
Benzocaine/Formula
How do you synthesis Benzocaine?
How do you synthesize P nitrobenzoic acid?
p-Nitrobenzoic acid can be prepared by the oxidation of p-nitrotoluene with nitric acid,1 chromic acid,2 permanganates,3 and electrolytically.
What is the role of h2so4 in ethyl p aminobenzoate benzocaine from P aminobenzoic acid?
What is para-aminobenzoic acid used for?
Para-aminobenzoic acid (PABA), also known as vitamin B10, is an organic compound found in certain foods and produced by the chemical industry. It was once added to sunscreen and has been used as a supplement to help darken gray hair and improve certain skin issues, among other uses.
Purpose: To prepare benzocaine (a local anesthetic) from p-aminobenzoic acid and ethanol, via a Fischer esterification reaction. Note: The ethanol used was denatured, and contained about 90% ethanol by weight.
What is the difference between benzocaine and ethyl 4-aminobenzoate?
It is a benzoate ester and a substituted aniline. Benzocaine is a Standardized Chemical Allergen. The physiologic effect of benzocaine is by means of Increased Histamine Release, and Cell-mediated Immunity. ethyl 4-aminobenzoate
What is the reaction between ethyl p-aminobenzoate and sodium carbonate?
Upon cooling, the reaction mixture sets to a solid mass of the hydrochloride of ethyl p-aminobenzoate. It is better, however, to pour the hot solution into 300 ml of water (no hydrochloride separates) and add solid sodium carbonate carefully to the clear solution until it is neutral to litmus.
What is the non-aqueous titration of benzocaine?
The American Chemical Society has specified a non-aqueous titration method [ 67]. Weigh approximately 150-170 mg of benzocaine into a 250 mL conical flask. Transfer 100 mL of acetic acid into the flask, and dissolve the benzocaine in the acid by placing the container in an ultrasonic bath at 20-25°C for 2-3 minutes.
