Fischer-Speier esterification

Esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. Oflen known as simply Fischer esterification.  

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 105, Springer International Publishing Switzerland 2014 

Often known as Fischer esterification , protic acid-catalyzed esterification of an acid and an alcohol. 

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Fig. 23(B) shows a modification of the reflux assembly to allow a gas to be passed through the boiling liquid cf. Fischer-Speier esterification, p. 104). The inlet-tube A fits into a three-necked adaptor shown in Fig. 22(J). The stopper B can be replaced by a dropping-funnel, etc.

The study of these fluorine-containing salts was then extended, and we prepared other new compounds in this series, e.g. 2-fluoroethyl glycine hydrochloride and 2-fluoroethyl betaine hydrochloride (that is, carbofluoroethoxy-methyl trimethyl ammonium chloride). The first of these was readily prepared by the Fischer-Speier esterification of glycine with fluoro-ethyl alcohol ... 

Fischer-Speier esterification method. Esterification of acids by refluxing with excess alcohol in the presence of hydrochloric acid or other acid catalysts. 

Fischer-Speier esterification to give a salt of an amino acid ester (by refluxing an alkanol with anhydrous HC1 or hot benzyl alcohol with toluene-/>-sulphonic acid) is straightforward. The fact that the nearby amino group is protonated when the carboxy group reacts to give a-amino acid esters does not slow the reaction down unduly a nearby positive site might have been expected to reduce the electrophilic character of the carboxy carbon atom. Without an acid catalyst, Walkylation can accompany esterification (Equation 4.6). 

Many acid catalysts have been employed in the Fischer-Speier esterification process, such as dry HC1,3-5 H2SO46-8 and MeSChH.9 Adams4 reported that esterification of acetonedicarboxylic acid 12 with alcohol 13 (saturated with HC1) provided the diester 14 in about 40% yield. 

Claisen-Schmidt reaction. Clemmensen reduction Darzens glycidic ester condensation Diazoamino-aminoazo rearrangement Dieclcmann reaction Diels-Alder reaction Doebner reaction Erlenmeyer azlactone synthesis Fischer indole synthesis. Fischer-Speier esterification Friedel-Crafts reaction... 

Other references related to the Fischer-Speier esterification are cited in the literature. ... 

Fischer s reagent reactivo de Fischer Fischer s salt sal de Fischer Fischer s solution solucidn de Fischer Fischer-Speier esterification method metodo de esterificacion de Fischer Speier Fischer-Tropsch process... 

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