Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. Experimental Procedures
3.2.1. General Procedure for the Esterification between Carboxylic Acids and Alcohols
3.2.2. Scale-Up Procedure for Preparation of Methyl Benzoate (1a) and Isolation of Succinimide
- Yield (methyl benzoate): 4.60 g, 85%.
- Yield (succinimide [57]): 272 mg, 98%.
- 1H NMR (300 MHz, CDCl3) δ 10.04 (s, 1H), 2.72 (s, 4H).
- 13C NMR (76 MHz, CDCl3) δ 178.8, 29.4.
3.2.3. Scale-Up Procedure for Preparation of Trimethyl Citrate (16a)
- Yield: 2.55 g, 99%.
3.2.4. Scale-Up Procedure for Preparation of Methyl Stearate (13a)
- Yield: 2.99 g, 100%.
3.2.5. Procedure for Recycling of N-bromosuccinimide (NBS) from Waste Succinimide
3.2.6. Detailed Procedures for the Preparation of Synthesized Compounds
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Entry | NXS | Loading [mol%] | Temperature [°C] | Conversion of Benzoic Acid to Methyl Benzoate [%] 2 |
---|---|---|---|---|
1 | / | / | 70 | 0 |
2 | NCS | 15 | 70 | 17 |
3 | NBS | 15 | 70 | 94 |
4 | NIS | 15 | 70 | 30 |
5 | NBS | 10 | 70 | 94 |
6 | NBS | 7 | 70 | 94 |
7 | NBS | 3 | 70 | 76 |
8 3 | NBS | 7 | 70 | <10 |
9 | NBS | 7 | 30 | 0 |
10 | NBS | 7 | 50 | 75 |
11 | NBS | 7 | 100 | 94 |
12 | HCl | 7 | 70 | 93 |
13 | HBr | 7 | 70 | 84 |
14 | HI | 7 | 70 | 68 |
15 | Br2 | 7 | 70 | 94 |
R2OH | R1 = Ph | R1 = Heptyl |
---|---|---|
Methyl Benzoates |
Methyl Alkyl Esters and Methyl Esters of Cholic Acid Derivatives |
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Čebular, K.; Božić, B.Đ.; Stavber, S. Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions. Molecules 2018, 23, 2235. https://doi.org/10.3390/molecules23092235
Čebular K, Božić BĐ, Stavber S. Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions. Molecules. 2018; 23(9):2235. https://doi.org/10.3390/molecules23092235
Chicago/Turabian StyleČebular, Klara, Bojan Đ. Božić, and Stojan Stavber. 2018. "Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions" Molecules 23, no. 9: 2235. https://doi.org/10.3390/molecules23092235