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Synlett 2018; 29(17): 2321-2325
DOI: 10.1055/s-0037-1610265
DOI: 10.1055/s-0037-1610265
letter
Na2CO3-Catalyzed O-Acylation of Phenols for the Synthesis of Aryl Carboxylates with Use of Alkenyl Carboxylates
The work was supported by the Youth Science and Technology Talent Development Project in the Education Department of Guizhou Province (Grant No. qianjiaohe KY zi [2016] number 263) and Innovation Team of Liupanshui Normal University (Grant No. LPSSYKJTD201601).Further Information
Publication History
Received: 14 July 2018
Accepted after revision: 09 August 2018
Publication Date:
31 August 2018 (online)
Abstract
Inorganic base-catalyzed O-acylation of phenol and its derivatives has been developed. The procedure provides an efficient catalysis system for the preparation of aryl carboxylates with alkenyl carboxylates as acyl reagents. The reaction proceeded smoothly by using Na2CO3 as the catalyst in MeCN to produce the corresponding aryl carboxylates in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610265.
- Supporting Information
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References and Notes
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- 13 General Procedure for the Synthesis of Aryl Carboxylates A mixture of phenol 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10 mmol, 20 mol%), and alkenyl carboxylate (2.0 mmol, 4.0 equiv) in MeCN (3 mL) was added to a Schlenk flask (25 mL) and stirred at r.t. The mixture was stirred at 120 °C until the reaction was finished. Then, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (petroleum ether/ethyl acetate 20:1 to 10:1) to afford the product 3. Naphthalen-2-yl Acetate (3aa) Yield: 99%, 92.8 mg, white solid, mp 70–72 °C. 1H NMR (400 MHz, CDCl3): δ = 7.81–7.72 (m, 3 H), 7.50 (d, J = 2.2 Hz, 1 H), 7.45–7.37 (m, 2 H), 7.19–7.15 (m, 1 H), 2.29 (s, 3 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 169.7, 148.3, 133.7, 131.4, 129.4, 127.8, 127.6, 126.6, 125.7, 121.1, 118.5, 21.2 ppm. HRMS: m/z calcd for C12H10O2Na [M + Na]+: 209.0578; found: 209.0582.