The Synthesis of Aldehydes from Carboxylic Acids

Abstract

The Rosenmund reduction of acid chlorides to the corresponding aldehydes was discussed in volume 4 of this series. There are a number of other less direct methods by which carboxylic acids can be converted into aldehydes and the purpose of this chapter is to consider the more useful of these procedures. Three of these methods, the hydrolytic decomposition of Reissert's compounds, the method of Grundmann, and the reductive desulfurization of thiol esters require acid chlorides as intermediates and in the respect are competitive with the Rosenmund reduction of acid chlorides. In the fourth method method, the McFadyen and Stevens synthesis, acid chlorides may be used for the preparation of the intermediate acyl hydrazides. Two additional methods, (Sonn and Muller, and Stephen) are based on the intermediate imido chlorides. These methods listed appear to be the one ones developed to the point where further discussion is profitable.

Partial reductions of carboxylic acids and their derivatives to aldehydes

“…Some of the reagents, for example, DIBAL-H, have been proven to be very reliable, and have been widely used by chemists to synthesize aldehydes from nitriles. [13][14][15][16][17][18][19][20][21][22][23][24] Since 2010, only two new reductions associated with this subtopic are available.…”

“…Reviews on reductive synthesis of aldehydes are available in the literature. The reviews in 1954, 13 1966, 14 and 1978 15 summarized the synthetic methods for preparing aldehydes from carboxylic acids and their derivatives. The review in 1978 was further updated in 1980, 16 1984, 17 1988, 18 1992, 19 and 2014.…”

Versatility of Supported Gold Nanoparticles on Hydrotalcites used for Oxidation and Reduction Reactions

“…Over the years, researchers have primarily focused on the oxidation of aldehydes to acids and not on the reverse reaction [6][7][8]. However, aldehydes (such as furfural (FF)) are one the most common building blocks used in fine chemicals synthesis (in the cosmetic, pharmaceutical, and agrochemical industry) [9]. They are conventionally produced following several techniques [10][11][12][13].…”

“…In the field of biocatalysis, the use of enzymatic catalysts, e.g., carboxylic acid reductase (CAR), promotes the conversion of fatty aldehydes to the corresponding fatty carboxylic acids avoiding the production of the corresponding alcohols [13,14]. The reduction of carboxylic acid has been extensively studied under conditions of non-catalytic and homogeneous catalytic reactions using different reducing agents [9][10][11][12]. The metal hydride-based reducing agents, such as lithium aluminum hydride, borane, and silanes, are generally used to produce aromatic aldehydes [15,16].…”

Evaluation of Hydroalcoholic Extract of Convolvulus pluriculis (Shankapushpi) for Standardization by Colorimetric Method: A Preliminary Report

“…Test for Carboxylic Acid Extract dissolved in water is treated with sodium bicarbonate. Brisk effervescence indicates the presence of carboxylic acid 27.…”