ex 10 synthesis of aspirin

aspirin

an odorless, white crystalline powder chemically known as 2-acetyloxybenzoic acid or acetylsalicylic acid (ASA)

2-acetyloxybenzoic acid or acetylsalicylic acid (ASA)

aspirin is chemically known as

aspirin

a weak acid that is only slightly soluble in water

aspirin

an aromatic compound with carboxylic acid and ester functional groups

aspirin

a known analgesic, antipyretic, anti- inflammatory drug

salicylic acid + acetic anhydride (in presence of acid catalyst)

synthetic production of aspirin

from willow bark oe meadow flowers

natural production of aspirin

aspirin

inhibit prostaglandin synthesis by irreversibly inactivating COX-1 and COX-2

Aspirin is said to inhibit thermoregulatory receptors in the hypothalamic center of the brain. Heat dissipation is a result of vasodilation and increased peripheral blood flow. But up to now, the exact MOA is unknown

1. analgesic and anti[inflammator

2. Antipyretic

3. ‘anti-thrombotoc

uses of aspiri

salicylic acid

limiting reactant in synethiss of aspirin

acetic anhydride

source of the acetyl group

deionized water

removes the water-soluble impurities such as acetic acid and sulfuric acid

petroleum ether

solvent used to wash the recrystallized aspirin crystals

esterification reaction

salicylic acid can react with acetic acid in an __ but the reaction is very slow, taking days to reach equilibrium, and the yield is low

vacuum filtration (Büchner filtration)

Aspirin crystals are filtered through

135C

melting point of aspirin

-

to determine the amount of aspirin in a sample, the precise volume and concentration of the sodium hydroxide, and the overall reaction, must be known

2-acetyloxybenzoic acid

IUPAC name of aspirin

C9H8O4

molecular formula of aspirin

180.16g/mol

molecular weight of aspirin

284C

bp of aspirin

135C

melting point of aspirin

0.25 g per 100 mL water at 15°C

solubility of aspirin

benzene with an attached carboxyl group and ester group on ortho position

structure of aspirin

-

aspirin does not have a phenol group

negative result

aspirin must yield a __ (a deep violet solution will not be observed) ferric chloride

the solution may turn to light purple due to presence of some salicylic acid (impurities in the aspirin)