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Synlett 2017; 28(08): 981-985
DOI: 10.1055/s-0036-1588399
DOI: 10.1055/s-0036-1588399
letter
Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
Further Information
Publication History
Received: 28 December 2016
Accepted after revision: 31 December 2016
Publication Date:
20 February 2017 (online)
Abstract
Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloroethane solvent with good catalytic activity.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588399.
- Supporting Information
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- 24 Ethyl 3-Phenylpropiolate (3a); Typical Procedure: A mixture of phenylpropiolic acid (1a; 0.2 mmol) and GO (50 wt%, calcd based on the mass of acid) in EtOH (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred and heated at 100 °C for 24 h. Upon completion of the reaction, GO was filtered, the solvent was removed, and the residue was separated by column chromatography (petroleum ether/ethyl acetate, 10:1) to give 1a (34 mg, 98%) as a yellow liquid. 1H NMR (400 MHz, CDCl3): δ = 7.63–7.54 (m, 2 H), 7.49–7.41 (m, 1 H), 7.41–7.32 (m, 2 H), 4.29 (q, J = 7.2 Hz, 2 H), 1.35 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 154.0, 132.9, 130.6, 128.5, 119.6, 86.0, 80.7, 62.1, 14.0. MS (EI): m/z = 174, 146, 129, 118, 102, 89, 75, 63, 51, 39, 29.
For some recent examples of GO as acid catalysts, see:
For selective recent examples, see: