2876-75-7Relevant academic research and scientific papers
Mild, one-pot conversion of carboxylic acids into esters using phase transfer catalysis
Puntambekar, Hemalata M,Naik, D G,Kapadi, A H
, p. 793 - 794 (2007/10/02)
One-pot conversion of carboxylic acids into esters under the influence of phase transfer catalysis is reported.The method is shown to work satisfactorily for optically active acids having epimerisable α-hydrogen.
Ester Homologation Revisited: A Reliable, Higher Yielding and Better Understood Procedure
Kowalski, Conrad J.,Reddy, Rajarathnam E.
, p. 7194 - 7208 (2007/10/02)
Enolate anions 3 and 6, prepared via enolization of α-bromo and dibromo ketones 4 and 5 were converted in high yield to ynolate anions 10 by respective addition of lithium tetramethylpiperidide (to effect deprotonation, 3 --> 7) or butyllithium (to effect metal-halogen exchange, 6 --> 7).Mixtures of such enolates were also obtainable from esters 1 on a large-scale (25 mmol) via in situ formation and addition of lithiodibromomethane (from methylene bromide and lithium tetramethylpiperidide), followed by treatment of the resulting adducts with lithiumhexamethyldisilazide to ensure complete enolization.Addition of sec-butyllithium and n-butyllithium to effect ynolate anion formation, followed by quenching of the reaction mixtures into acidic ethanol, reproducibly afforded homologated esters 8 in 67-90percent yield.Demonstrated for ethyl esters 1 having the carbethoxy moiety attached to primary, secondary, tertiary, aryl, and alkenyl groups, this general procedure provides a convenient, large-scale alternative to the classical Arndt-Eistert sequence.
Mono- and Bi-metallic Catalysed Formate-Halide Carbonylation Reactions
Buchan, Caroline,Hamel, Nathalie,Woell, James B.,Alper, Howard
, p. 167 - 168 (2007/10/02)
Benzylic, aryl, and alkyl halides react with formate esters and carbon monoxide, in the presence of the dimer of chloro(hexa-1,5-diene)rhodium(I), 2, to give carboxylic esters: bimetallic catalysis 2> is particularly beneficial when an aromatic halide is used as the substrate.
