synthesis of acetylsalicylic acid Flashcards
Active extract
(willow bark)
scientific name of white willow
(Salix alba)
Latin name of Salicylic acid
salicin
ortho to the carboxyl group
C6H4(OH)COOH - OH group
salicylic acid also known as
2-hydroxybenzoic acid
solubility in water
Poorly soluble
solubility in ethyl ether, chloroform, benzene, acetone, turpentine oil
soluble
PHYSICAL PROPERTIES of salicylic acid
White crystalline powder, first bitter taste the sweet
Pungent odor
Melting point of salicylic acid
158.6 °C
5 USES of salicylic acid
Food additive
Flavoring agent
Synthesis of ASA
Starting material for other pharmaceutical products (esters, amides)
intermediate in the production of agrochemical products (dyes
and colorants, rubber industry)
PHARMACEUTICAL USES:
● Keratolytic agent
● Analgesic
● Antipyretics and anti-inflammatory
unbuffered (without chemicals to keep stable) formulations and tend to have greater impact on the skin.
Natural salicylic acid
Benefits: of natural salicylic acid
does not increase the blood vessels in the skin like some other acids.
Agents require buffering (stabilizing of the acidity pH) using chemical agents in order to stabilize
Synthetic acid agents
Common salicylate-containing medicines
bismuth subsalicylate choline salicylate diflunisal magensium salicylate slasalate
(IUPAC name of salicylic acid)
*2-hydroxybenzoic acid
(IUPAC name of salicylic acid)
2-hydroxybenzoic acid
chemical reaction involved in synthesis of salicylic acid
Methyl Salicylate + NaOH → Disodium Salicylate + H2SO4 → Salicylic Acid
Reaction with Bromine Water:
milky white color
Reaction with Ferric Chloride Solution:
(blue or violet) complexes
Reaction with methyl alcohol:
Minty smell
combination of salicylic acid and methanol
methyl salicylate or oil of wintergreen.
AKA: methyl alcohol and wood alcohol
when salicylic acid is treated with the bromine water it leads to the formation of
and this reaction is known as
2,4,6 – tribromophenol
bromination of salicylic reaction
