Acetoxypropionic acid

This standard was obtained in two ways. An asymmetric hydroformylation was run and the aldehyde was oxidized to S-a-acetoxypropionic acid. A comparison of the rotation obtained with the literature (19) for pure S-acid [a] )0 = -49.3°C (7.2, CHC13) was used to arrive at the 34.9°C figure for pure S-aldehyde. This number was checked using an NMR shift reagent. 

The by-product, (3-acetoxypropionic acid, may be thermally decomposed to yield more acrylic acid ... 

C5H804 a-acetoxypropionic acid 535-17-1 443.90 38.521 2 5042 C5H9CI 4-chloro-2-methyl-1 -butene 10523-96-3 375.15 32.030 1,2... 

In acetic acid as solvent, acrylic acid is produced (eq. (31)), accompanied by some acetoxypropionic acid [114]. 

L-2-Acetoxypropionic acid (123) is readily prepared by the acylation of L-lactic acid with either acetic acid/sulfuric acid in benzene (50% yield) [79] or with an excess of acetyl chloride (80% yield) [80]. One is not limited exclusively to the use of lactic acid as the starting material. Diazotization of L-alanine in acetic acid furnishes 123 in 47% yield with at least 96% retention of configuration [48]. 

S-Acetoxypropionic acid 2-Hydroxypropanoic acid acetate Acetyllactic acid... 

The suggested mechanism (Scheme 11) involves migratory insertion of coordinated ethylene into a palladium-carboxyl bond formed by the reaction of the Pd—CO species with water. Acrylic acid results from j8-hydride elimination of the carboxypalladation intermediate, whereas oxidative cleavage by AcOH results in the formation of j8-acetoxypropionic acid. ... 

Bruns, R., Jones, D.T., Ritchie, P.D., 1935. The pyrolysis of derivatives of a-acetoxypropionic acid, and related substances. Jorunal Chemical Society 400-406. 

Ratchford and Fisher found that methyl-acetoxypropionate decomposes on heating to form acetic acid and methyl acrylate ... 

Similar straight-line correlations between aqueous solubility and Nc or M have been found for certain homologous series of mono- and multifunctional compounds such as 1-alkanols, 2-alkanols [6], 2-alkanones [9], n-alkyl acetates [10], n-alkyl /3-ethoxypropionates [11], n-alkyl a-acetoxypropionates, and n-alkyl lactates [12]. In contrast, Sobotka and Kahn [13] have found significant deviations from simple linear correlations with Nc for the series of ethyl esters of monocarbonic acids. They report a zig zag curve caused by the relatively higher solubility of the members with odd values for Nq- The odd-even effect is discussed in detail by Burrows [14], with further examples provided. 

Esters of acrylic acid are made by pyrolytic decomposition of a-acetoxypropionates. Direct dehydration of the a-hydroxy esters fails. 

The catalyst system contains several additives, including chlorides of lithium, sodium, rhenium, etc., and lithium or sodium acetate dihydrate. The main by-products are -acetoxypropionic arid, which is mainly formed if acetic acid is employed as a solvent ... 

It is prepared by the reaction of 2-acetoxypropion aldehyde with acetic add anilide in benzenic medium in the presence of sulfuric acid (Merkle and Siegel,... 

E14.9 Let us consider the methyl acetoxypropionate decomposition that forms methyl acrylate and acetic acid according to the reaction ... 

Rehberg, C.E., Faucette, W.A., Fisher, C.H., 1944. Preparation of methyl acetoxypropionate reaction of lactic acid with methyl acetate. Industrial Engineering Chemistry 36,469-472. 

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