The Friedel Crafts Reaction: Anthraquinone - Experiment | CHEM 210, Lab Reports of Organic Chemistry

Download The Friedel Crafts Reaction: Anthraquinone - Experiment | CHEM 210 and more Lab Reports Organic Chemistry in PDF only on Docsity! Introduction: The Friedel-Crafts reaction of phthalic anhydride with excess benzene as solvent and two equivalents of aluminum chloride proceeds rapidly and gives a com- plex salt of 2-benzoylbenzoic acid in which one mole of aluminum chloride has reacted with the acid to form the salt RCO2- . AlCl2+ and a second mole is bound to the car- bonyl group. On addition of ice and hydrochloric acid, the complex is decomposed and basic alumi- num salts are brought into solution. Treatment of 2-benzoylbenzoic acid with concentrated sulfuric acid effects cyclodehy- dration to anthraquinone, a pale-yellow, high-melting compound of great stability. Be- cause anthraquinone can be sulfonated only under forcing conditions, a high tempera- ture can be used to shorten the reaction time without loss in yield of product; the con- ditions are so adjusted that anthraquinone separates from the hot solution in crystal- line form, which favors rapid drying. . T H E F R I E D E L - C R A F T S R E A C T I O N : A N T H R A Q U I N O N E C H E M 2 1 0 / 2 1 2 R E A C T I O N S C O V E R E D > Electrophilic Aro- matic Substitution C H E M 2 1 3 EXPERIMENT 64 Spring 2009 from K. L. Williamson,  Macroscale and Microscale  Organic Experiments, 2nd  Ed. 1994, Houghton Mifflin,  Boston p449; revised 1/09