Name: synthesis of esters via a greener steglich esterification in acetonitrile
Uploaded: 2018-10-30T15:00:00
Description: Watch this Scientific Journal Video about Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile at JoVE.com

This research was supported by Siena College and the Center for Undergraduate Research and Creative Activity. We thank Dr. Thomas Hughes and Dr. Kristopher Kolonko for helpful conversations, Ms. Allycia Barbera for early stage work on this methodology, and the Siena College Stewart&#39;s Advanced Instrumentation and Technology (SAInT) Center for instrumentation resources.

Caution: Consult Safety Data Sheets (SDSs) prior to the use of the chemicals in this procedure. Use appropriate personal protective equipment (PPE) including splash goggles, lab coat, and nitrile or butyl gloves as many of the reagents and solvents are corrosive or flammable. Carry out all reactions in a fume hood. It is unnecessary to dry glassware or to use a nitrogen atmosphere for this protocol.
1. Carbodiimide Coupling Reaction for Primary Alcohols
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	<li>In a 50 mL round bottom flas...

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The methodology presented here was developed to minimize the hazards from solvent associated with a traditional Steglich esterification by using a greener solvent system and by reducing the need for column chromatography8,9. Comparable reaction yields and rates can be achieved with the use of acetonitrile in place of dry chlorinated solvents or DMF22.
Several key steps enable the efficient purification of produc...

Ester compounds are widely used for the applications such as flavor compounds, pharmaceuticals, cosmetics, and materials. Commonly, the use of carbodiimide coupling reagents is used to facilitate an ester formation from a carboxylic acid and an alcohol1. For example, in the Steglich esterification, dicyclohexylcarbodiimide (DCC) is reacted with a carboxylic acid in the presence of 4-dimethylaminopyridine (DMAP) to form an activated acid derivative, generally in a chlorinated solvent system or dimethylformamide (DMF)2,3,4. The activated acid derivative then undergoes a nucleophilic acyl substitution with an alcohol to form the ester product, which is usually purified via chromatography. The Steglich esterification enables mild coupling of large, complex carboxylic acids and alcohols, including sterically hindered secondary and tertiary alcohols2,5,6. The goal of this work is to modify the standard Steglich esterification protocol to provide a greener synthetic option for this common esterification reaction.
One important aspect in the design of new synthetic methodology is to seek to minimize the use and formation of hazardous substances. The Twelve Principles of Green Chemistry7 can be used to provide a guideline for creating safer syntheses. Some of these include the prevention of waste generation (Principle 1) and the use of safer solvents (Principle 5). In particular, solvents account for 80-90% of the non-aqueous mass of the materials in pharmaceutical manufacturing8. Thus, modifying a protocol to use a less hazardous solvent can make a large impact on the greenness of an organic reaction.
Steglich esterification reactions often use anhydrous chlorinated solvent systems or DMF; however, these solvents are of concern for both the environment and human health. Dichloromethane (CH2Cl2) and chloroform (CHCl3) are probable human carcinogens, and DMF has reproductive toxicity concerns9. In addition, CH2Cl2 is ozone depleting10. Thus, a less hazardous solvent for the Steglich esterification would be of great utility. While there are not yet green replacements for polar aprotic solvents, acetonitrile is recommended as a greener replacement for CH2Cl2, CHCl3, and DMF9. Acetonitrile is currently produced as a byproduct in acrylonitrile manufacturing; however, a green synthesis of acetonitrile from biomass on an academic scale has been reported11, and potential options for the reuse and recovery from waste streams are being investigated12. Acetonitrile has previously been used as a greener solvent alternative for carbodiimide coupling reactions in solid-phase peptide synthesis to form amide linkages13. The use of acetonitrile as a solvent system for Steglich esterifications has been demonstrated14,15,16,17,18,19,20,21; however, these methods have not focused on the green aspect of the solvent and also employ additional purification via column chromatography.
Reducing the need for column chromatography as a purification step also minimizes hazardous solvent waste8. In addition to using a less hazardous reaction solvent, the methodology enables the isolation of highly pure product without the need for chromatography. The traditionally used dicyclohexylcarbodiimide (DCC) coupling reagent is substituted with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC). The basic amine functional group on this reagent enables the reaction byproducts and any residual reagents to be removed via acidic and basic wash steps.
The protocol presented herein can be used with a variety of acid and alcohol partners (Figure 1). It was used to synthesize a small library of cinnamyl ester derivatives using primary, secondary, benzyl, and allyl alcohols and phenols22. Additionally, the rate of the esterification reaction in acetonitrile is comparable to that in the chlorinated and DMF solvent systems, without a need to dry or distill the acetonitrile prior to the reaction22. Esters synthesized from tertiary alcohols have not been isolated, which is currently a limitation of the methodology compared to the traditional Steglich esterification in chlorinated solvent23. In addition, other acid-labile groups could be affected by the acid wash steps, potentially necessitating column chromatography for purification after acetonitrile removal. Despite these limitations, the reaction is a facile and general method for the synthesis of esters in high yields using a range of both alcohol and carboxylic acid components. The use of a greener solvent system and high purity without the need for chromatography steps make this protocol an attractive alternative to a traditional Steglich esterification.
<img alt="Figure 1" class="xfigimg" src="/files/ftp_upload/58803/58803fig1.jpg" /> 
Figure 1. General reaction scheme. The general scheme for the reaction involves the coupling of a carboxylic acid and an alcohol, which is facilitated using a carbodiimide coupling reagent (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, or EDC) and 4-dimethylaminopyridine (DMAP) in acetonitrile. To demonstrate the reaction breadth, esters were formed using various acids (1-5) with either a primary (6) or secondary (7) alcohol. <a href="https://www.jove.com/files/ftp_upload/58803/58803fig1large.jpg" target="_blank">Please click here to view a larger version of this figure.</a>

<table>
	<tbody>
		<tr>
			<td>trans -cinnamic acid</td>
			<td>Acros Organics</td>
			<td>158571000</td>
			<td></td>
		</tr>
		<tr>
			<td>butyric acid</td>
			<td>Sigma-Aldrich</td>
			<td>B103500</td>
			<td>Caution: corrosive</td>
		</tr>
		<tr>
			<td>hexanoic acid</td>
			<td>Sigma-Aldrich</td>
			<td>153745-100G</td>
			<td>Caution: corrosive</td>
		</tr>
		<tr>
			<td>decanoic acid</td>
			<td>Sigma-Aldrich</td>
			<td>21409-5G</td>
			<td>Caution: corrosive</td>
		</tr>
		<tr>
			<td>phenylacetic acid</td>
			<td>Sigma-Aldrich</td>
			<td>P16621-5G</td>
			<td></td>
		</tr>
		<tr>
			<td>3-methoxybenzyl alcohol</td>
			<td>Sigma-Aldrich</td>
			<td>M11006-25G</td>
			<td></td>
		</tr>
		<tr>
			<td>diphenylmethanol</td>
			<td>Acros Organics</td>
			<td>105391000</td>
			<td>Benzhydrol</td>
		</tr>
		<tr>
			<td>chloroform-d</td>
			<td>Acros Organics</td>
			<td>166260250</td>
			<td>99.8% with 1% v/v tetramethylsilane, Caution: toxic</td>
		</tr>
		<tr>
			<td>hexane</td>
			<td>BDH Chemicals</td>
			<td>BDH1129-4LP</td>
			<td>Caution: flammable</td>
		</tr>
		<tr>
			<td>ethyl acetate</td>
			<td>Sigma-Aldrich</td>
			<td>650528</td>
			<td>Caution: flammable</td>
		</tr>
		<tr>
			<td>diethyl ether</td>
			<td>Fisher Scientific</td>
			<td>E138-500</td>
			<td>Caution: flammable</td>
		</tr>
		<tr>
			<td>acetonitrile</td>
			<td>Fisher Scientific</td>
			<td>A21-1</td>
			<td>ACS Certified, &#62;99.5%, Caution: flammable</td>
		</tr>
		<tr>
			<td>4-dimethylaminopyridine</td>
			<td>Acros Organics</td>
			<td>148270250</td>
			<td>Caution: toxic</td>
		</tr>
		<tr>
			<td>magnesium sulfate</td>
			<td>Fisher Scientific</td>
			<td>M65-3</td>
			<td></td>
		</tr>
		<tr>
			<td>hydrochloric acid, 1 M</td>
			<td>Fisher Scientific</td>
			<td>S848-4</td>
			<td>Caution: corrosive</td>
		</tr>
		<tr>
			<td>sodium chloride</td>
			<td>BDH Chemicals</td>
			<td>BDH8014</td>
			<td></td>
		</tr>
		<tr>
			<td>sodium bicarbonate</td>
			<td>Fisher Scientific</td>
			<td>S25533B</td>
			<td></td>
		</tr>
		<tr>
			<td>1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride</td>
			<td>Chem-Impex</td>
			<td>00050</td>
			<td>Caution: skin and eye irritant</td>
		</tr>
		<tr>
			<td>thin layer chromatography plates</td>
			<td>EMD Millipore</td>
			<td>1055540001</td>
			<td>aluminum backed sheets</td>
		</tr>
		<tr>
			<td>Note: All commercially available reagents and solvents were used as received without further purification.</td>
			<td></td>
			<td></td>
			<td></td>
		</tr>
	</tbody>
</table>

synthesis of esters via a greener steglich esterification in acetonitrile

The Steglich esterification is a widely-used reaction for the synthesis of esters from carboxylic acids and alcohols. While efficient and mild, the reaction is commonly performed using chlorinated or amide solvent systems, which are hazardous to human health and the environment. Our methodology utilizes acetonitrile as a greener and less hazardous solvent system. This protocol exhibits rates and yields that are comparable to traditional solvent systems and employs an extraction and wash sequence that eliminates the need for the purification of the ester product via column chromatography. This general method can be used to couple a variety of carboxylic acids with 1&#176; and 2&#176; aliphatic alcohols, benzylic and allylic alcohols, and phenols to obtain pure esters in high yields. The goal of the protocol detailed here is to provide a greener alternative to a common esterification reaction, which could serve useful for ester synthesis in both academic and industrial applications.

Using the modified Steglich esterification in acetonitrile followed by an acid-base extraction workup, 3-methoxybenzyl cinnamate (8) was obtained as a light-yellow oil (205 mg, 90% yield) without the need for column chromatography. 1H and 13C NMR spectra are presented in Figure 2 to confirm the structure and to indicate purity.
Compounds 9-<str...

Watch this Scientific Journal Video about Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile at JoVE.com

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

A modified Steglich esterification reaction was used to synthesize a small library of ester derivatives with primary and secondary alcohols. The methodology uses a non-halogenated and greener solvent, acetonitrile, and enables product isolation in high yields without the need for chromatographic purification.

The Steglich esterification is a widely-used reaction for the synthesis of esters from carboxylic acids and alcohols. While efficient and mild, the ...

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