ORGANIC SYNTHESIS OF CAFFEINE 3,7-dihydro-1,3,7- trimethyl-1H-purine-2,6-dione

Mark Zakariya, Erica Hoey, Daniel Kim, Jeffrey Chyau4/6/2009

Outline (FIX ME FIX ME FIX ME) Background of Friedrich Ferdinand

Runge Discovery of the Synthesis of Caffeine Applications/Uses of Caffeine Impact of caffeine on Society Physical and Chemical Properties of

Caffeine Synthesis Steps required to synthesize caffeine Bibliography (ALA)

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Background of Friedrich Ferdinand Runge

German analytical chemist Famously discovered various substances,

including: Caffeine The blue dye aniline A variety of coal tar products Paper chromatography

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Discovery and Synthesis of Caffeine

Friedrich Ferdinand Runge extracted caffeine from a box of Arabian Mocha beans.

His method was paper chromatography (similar to TLC used in this class).

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+ =

Arabian Mocha Beans Paper Chromatography Caffeine

Applications/Uses of Caffeine Caffeine is a psychoactive (mind-

affecting) drug that serves as a stimulant.

Caffeine is a mild diuretic. Caffeine is used in headache

medications.

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Impact of Caffeine on Society Caffeine is the most widely used

psychoactive substance in the world. In Western society, at least 80% of

adults consume enough caffeine to have effects on the brain.

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Impact of Caffeine on Society (cont.’d)

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Impact of Caffeine on Society (cont.’d)

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Impact of Caffeine on Society (cont.’d)

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Physical and Chemical Properties of Caffeine Synthesis

Caffeine appears as a white, odorless powder

Density: 1.23 g·cm−3

Melting point: 227-228°C Boiling point: 178°C

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Organic Synthesis of Caffeine

USP-Grade Caffeine

Synthesis of Caffeine

Dimethyl-uric acid treated with trichloride + oxychloride of phosphorus (150°C) Chlorotheophylline

In the process, a hydroxyl group is replaced by one chlorine atom

ChlorotheophyllineDimethyl-uric acid

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Organic Synthesis of Caffeine

Synthesis of Caffeine (cont.’d)

Hydriotic acid used to reduce chlorotheophylline into theophylline

Then, methyl iodide and theophylline react to produce caffeine

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Organic Synthesis of Caffeine

Extraction of Caffeine

Caffeine is relatively difficult to synthesize.

Caffeine is readily available in a variety of plants, such as the kola nut.

Over 90% of caffeine in beverages and medicines are obtained from “decaffeinated” products such as teas and coffees.

Decaffeination processes: Swiss water process, Direct Method, Indirect Method, Supercritical Fluid Extraction, and the Triglyceride Process.

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Organic Synthesis of Caffeine

Extraction of Caffeine (cont.’d)

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