Green Esterification of Carboxylic Acids Promoted bytert‐Butyl Nitrite

Abstract

In this work, the green esterification of carboxylic acids promoted by tert‐butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Halogenation Reactions of Alkyl Alcohols Employing Methyl Grignard Reagents

“…TLC R f = 0.4 (30% EtOAc/hexanes, KMnO 4 stain); 1 H NMR (400 MHz, CDCl 3 ) δ 3.66 (s, 3H), 3.66–3.57 (m, 1H), 2.35 (ddd, J = 15.4, 10.3, 5.2 Hz, 1H), 2.27–2.17 (m, 1H), 1.95 (ad, J = 11.9 Hz, 1H), 1.91–1.70 (m, 5H), 1.66 (ad, J = 12.9 Hz, 1H), 1.61–1.47 (m, 2H), 1.46–0.85 (m, 24H), 0.64 (s, 3H). Analytical data is consistent with literature values …”

“…Analytical data is consistent with literature values. 66 Iodide 29 was prepared according to a modified Method C. The following amounts of reagents were used: alcohol 67 (0.16 g, 0.40 mmol, 1.0 equiv), MsCl (47 μL, 0.60 mmol, 1.5 equiv), Et 3 N (84 μL, 0.60 mmol, 1.5 equiv), DCM (2.0 mL, 0.20 M in substrate), MeMgI (0.27 mL, 0.80 mmol, 2.0 equiv, 3.0 M in Et 2 O), PhMe (2.0 mL, 0.20 M in substrate). Upon addition of MeMgI, the reaction mixture was allowed to stir at 0 °C for 1 h. The residue was purified by column chromatography (0−10% EtOAc/hexanes) to afford the title compound as a white solid (0.17 g, 0.33 mmol, 83% yield).…”

Use of dipyridyldithiocarbonate (DPDTC) as an environmentally responsible reagent leading to esters and thioesters under green chemistry conditions

“…Although other "green" methodologies are available and have been developed en route to esters and thioesters, [24][25][26][27][28][29][30][31] including a solvent-reagent selection guide to identify the most sustainable combination, improvements can be anticipated. 10a,b Hence, in this report are described green and efficient approaches to esterification and thioesterification that make use of an in situ-formed and used (albeit stable and isolable) 2-pyridylthioester intermediate.…”

Isobaric Vapor–Liquid Equilibrium of Isoamyl Alcohol, Cyclohexane, n-Hexane, and the n-Heptane + Isoamyl Butyrate Binary System at 101.3 kPa

“…The amount of entrainers, cost, impacts on the environment, and the ease of separation from the product are also important indicators for the choice of entrainers. − The common entrainers in the synthesis of isoamyl butyrate are n -hexane, cyclohexane, isoamyl alcohol, and n -heptane. In order to make the production process of ester products a truly green chemical industry, how to select, use, and deal with the problem of entrainers in the esterification reaction will surely arouse people’s general attention. , …”

“…In order to make the production process of ester products a truly green chemical industry, how to select, use, and deal with the problem of entrainers in the esterification reaction will surely arouse people's general attention. 18,19 The vapor−liquid equilibrium (VLE) data play an important role in practical production and are an important basis for the chemical process design and simulation. 20,21 There are many papers studying the vapor−liquid equilibrium data of n-hexane, cyclohexane, isoamyl alcohol, and n-heptane.…”