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Group 7, Chem 31.1, AB2,

Atienza, Von Ervy; Alcantara, Mark Jun

Sir Kevin Sison

May 24, 2010

Abstract
Organic synthesis is a branch of chemical synthesis dealing with the production of organic compoundsby organic
reactions. Aspirin is one of the most widely used analgesics since its invention in 1853. The mainobjective of this experiment is
to produce acetylsalicylic acid via esterification. Aspirin (wanted product) andacetic acid (by product) w ere produced by reacting
salicylic acid with acetic anhydride and catalyzed usingphosphoric acid. After the reaction, the products were recrystallized to
enhance the purity of the resultingcompound. The product was then subjected to physical and chemical t ests and the results
obtained wererecorded. Several methods and information regarding organic reactions learned from previous experimentswere
used.

Keywords: Synthesis, Acetylsalicylic acid, Salicylic acid, Esterification, Recrystallization, Suction Filtration

Introduction
Organic synthesis is a special branch ofchemical synthesis and is concerned with theconstruction of organic
compounds via organicreactions. Organic molecules can often contain ahigher level of complexity compared to purelyinorganic
compounds, so the synthesis of organiccompounds has developed into one of the mostimportant aspects of organic chemistry.
In theexperiment product synthesized was acetylsalicylicacid, known as aspirin.
Acetylsalicylic acid, commonly known asaspirin is used as an analgesic to relieve minoraches and pains, as an
antipyretic to reduce fever,and as an anti -inflammatory medication. It isstructurally related to salicylic acid. As can be seenfrom
the figure in the below, salicylic acid is both aphenol and an aromatic carboxylic acid. Comparingthe two compounds, it can be
observed that aspirinis an ester, formed between acetic acid and thephenol hydroxyl group of salicylic acid. Thecarboxylic ac id
group makes aspirin mildly acidic.Its aromatic ring causes it to be quite insoluble inwater. Aspirin can be made soluble by
forming itssodium salt. Salicylic acid reacts with aceticanhydride when phosphoric acid is present as acatalyst. Once the asp irin
is synthesized, it can becollected by suction filtration while the more watersoluble unreacted starting materials are washedaway
in the aqueous solvent. At this point theproduct is already isolated. To purify your productfurther, it is necessary to recry stallize
the crudeaspirin.

Experimental

Production of Aspirin
Two grams of salicylic acid, 5 ml aceticanhydride and 5 drops of 85% phosphoric acidwere placed in a 125-mL
Erlenmeyer flask andstirred. The flask was heated in a boiling water bathfor 5 minutes. Then the flask was removed from
thebath and, while still hot, 2 ml of cold water wascautiouslyaddedtoit.After Complete decomposition, 40 ml of water was added
to it, it isthen stirred until crystals have begun forming. Themixture was cooled in an ice bath to completerecrystallization . The
product was collected bysuction filtration, washed with 5 ml of cold waterand then dried. The product was recrystallized from35
ml of hot water and decolorized using activatedcarbon (if the product was colored). It was thendried and weighed.

Test for the Product

a.Physical Test: The appearance, texture,color, and odor of the product were recorded. Its melting point was also determined