The Preparation of High Molecular Weight Acyloins

Hansley, V. L.

doi:10.1021/ja01314a076

Cited by 38 publications

(9 citation statements)

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“…For comparison (and to confirm our methodology), the intermolecular reaction between methyl hexanoate was carried out using fine sodium sand in refluxing toluene under nitrogen and 7 was then isolated in 68% yield. A similar yield (80%) was reported for this reaction when it was carried out in refluxing xylene (7). All the remaining condensation reactions were performed in the presence of TMSCl (8).…”

Section: + 'supporting

confidence: 76%

The acyloin reaction using tethered diesters

Daynard¹,

Eby²,

Hutchinson³

1993

Can. J. Chem.

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A study of the intramolecular acyloin condensation using diesters tethered by their alkoxide groups was undertaken. The goal was to provide a method for optimizing the yield of mixed acyloin products from the reaction of two different esters by utilizing tethered dissimilar esters as substrates. The results of the study show that the yield of the acyloin condensation is dependant on the tether length. Tethers of 8 and 14 carbons in length give yields comparable to those obtained from an intermolecular control reaction while shorter tethers give reduced yields of product. However, the use of mixed tethered diesters and a crossover experiment between two different tethered substrates provides a statistical distribution of products. These observations have been interpreted as resulting from a fragmentation of the initially formed radical anion intermediate that destroys the tethered nature of the substrate(s).

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Section: + 'supporting

confidence: 76%

The acyloin reaction using tethered diesters

Daynard¹,

Eby²,

Hutchinson³

1993

Can. J. Chem.

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“…Our approach is based on the acyloin condensation of methyl 10-undecenoate 2. This reaction, coupling two (identical) esters by means of molten sodium in a refluxing solvent, has already been reported in 1935 by Hansley [15]. He synthesized acyloins or hydroxyketones from long-chain aliphatic esters containing 8-18 carbon atoms by reacting them with finely dispersed sodium in boiling xylene, a reaction that was until then limited to esters of six or less carbon atoms.…”

Section: Introductionmentioning

confidence: 64%

Undecylenic acid: A valuable renewable building block on route to Tyromycin A derivatives

Steen

Stevens

Eeckhout

et al. 2008

Euro J Lipid Sci & Tech

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A key intermediate for the synthesis of Tyromycin A, a C-20 tetrachlorodicarboxylic acid, was produced in six steps starting with the dimerization of methyl 10-undecenoate which was obtained from a renewable resource, e.g. castor oil. The acyloin condensation product was then oxidized, transformed to the diene, followed by ozonization, chlorination and finally oxidation to the corresponding tetrachlorodicarboxylic acid.

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“…2-Hydroxy-5-methylbenzophenone 1 k has been obtained in the reaction of p-cresole with benzylidyne chloride in the way described by KEWMAN [2]. 5, R-Diethyl-7-hydroxy-6-dodecanone 11 was received by acyloin condensation [3].…”

Section: Experiments A1mentioning

confidence: 99%