Experiment 9- Synthesis of Organic Compounds [Aspirin] Group 7, Chem 31.1, AB2,Atienza, Von Ervy; Alcantara, Mark JunSir Kevin SisonMay 24, 2010Abstract
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) were 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 tests and the results obtained wererecorded. Several methods and information regarding organic reactions learned from previous experimentswere used.
Synthesis, Acetylsalicylic acid, Salicylic acid, Esterification, Recrystallization, Suction Filtration
Organic synthesis is a special branch of chemical 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 minor aches 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 acid 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 aspirin is synthesized, it can becollected by suction filtration while the more water soluble unreacted starting materials are washedaway in the aqueous solvent.
At this point theproduct is already isolated. To purify your productfurther, it is necessary to recrystallize the crudeaspirin.
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 wascautiously added to it. After completedecomposition, 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 water and 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 wererecorded. Its melting point was alsodetermined.