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Was this experiment green and were the solvents safe? Could other have alternatives been used (including less solvent)? Was this energy Intensive?

Was this experiment green and were the solvents safe? Could other have alternatives been used (including less solvent)? Was this energy Intensive?

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.28P
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Was this experiment green and were the solvents safe? Could other have alternatives been used (including less solvent)? Was this energy Intensive?
Ally CHE 251L Experiment 1: Isolation of Guaifenesin from a Tablet Adapted from Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets, J. Chem Ed, 2003 There are classic reactions thatáre covered in the introductory organic chemistry curriculum. The synthesis of an ether from an alhalide and an alkoxide is one such reaction and is known as the Williamson ethersynthesis. We encountered this reaction in Chapter 9 of the text, and it is introduced formally in Chapter 10 (Section 10-6). The reaction proceeds via an S,2 mechanism. it is paramount that the alkyl halide be sterically unhindered. Ly Slow reaction î E In striving to keep the course relevant to your interests, we are going to work with a clinically relevant compound for the next two weeks, guaifenesin. Guaifenesin is an expectorant, that is used to alleviate cold symptoms. The structure is shown below. HO но OH OH (R)-(-)-guaifenesin (S)-(+)-guaifenesin Note that this compound has one stereogenic center, and two ether functional groups. The first week of the experiment, we will isolate a racemic mixture of the compound from a commercial tablet. You will characterize the tablet using its melting point, 1H NMR and IR data. The idea is to familiarize yourselves with the pure compound before attempting the synthesis. The second week, we will synthesize a racemic mixture using a phenoxide and alkyl halide. Procedure: Isolation of Guanefesin A single Guai-Aid tablet (containing 600 mg (±) guaifenesin) is crushed to powder and added to 5 mL ethyl acetate. The suspension is stirred at room temperature for 10 min and any insoluble material removed by gravity filtration., Addition of 10 mL hexanes to the filtrate in 2-mL portions causes white crystais to form on standing for a few min. After cooling in an ice-bath the precipitate is collected by vacuum filtration and washed with 5 mL cold hexanes. Obtain a melting point, 'H NMR spectrum, and IR spectrum of the isolated compound.
Transcribed Image Text:Ally CHE 251L Experiment 1: Isolation of Guaifenesin from a Tablet Adapted from Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets, J. Chem Ed, 2003 There are classic reactions thatáre covered in the introductory organic chemistry curriculum. The synthesis of an ether from an alhalide and an alkoxide is one such reaction and is known as the Williamson ethersynthesis. We encountered this reaction in Chapter 9 of the text, and it is introduced formally in Chapter 10 (Section 10-6). The reaction proceeds via an S,2 mechanism. it is paramount that the alkyl halide be sterically unhindered. Ly Slow reaction î E In striving to keep the course relevant to your interests, we are going to work with a clinically relevant compound for the next two weeks, guaifenesin. Guaifenesin is an expectorant, that is used to alleviate cold symptoms. The structure is shown below. HO но OH OH (R)-(-)-guaifenesin (S)-(+)-guaifenesin Note that this compound has one stereogenic center, and two ether functional groups. The first week of the experiment, we will isolate a racemic mixture of the compound from a commercial tablet. You will characterize the tablet using its melting point, 1H NMR and IR data. The idea is to familiarize yourselves with the pure compound before attempting the synthesis. The second week, we will synthesize a racemic mixture using a phenoxide and alkyl halide. Procedure: Isolation of Guanefesin A single Guai-Aid tablet (containing 600 mg (±) guaifenesin) is crushed to powder and added to 5 mL ethyl acetate. The suspension is stirred at room temperature for 10 min and any insoluble material removed by gravity filtration., Addition of 10 mL hexanes to the filtrate in 2-mL portions causes white crystais to form on standing for a few min. After cooling in an ice-bath the precipitate is collected by vacuum filtration and washed with 5 mL cold hexanes. Obtain a melting point, 'H NMR spectrum, and IR spectrum of the isolated compound.
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Guaifenesin is synthesized by Guaicol in an SN2 reaction with NaOH which provides conjugate base of Gauicol which is then dissolved in a solution of 3-chloro1,2-propanediol to form Guaifenesin and the reaction falls under the category of Williamson-ether synthesis.

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