2007
DOI: 10.1055/s-2007-983746
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Simple and Effective Protocol for Claisen-Schmidt Condensation of Hindered Cyclic Ketones with Aromatic Aldehydes

Abstract: A simple and effective methodology for ClaisenSchmidt condensation of (-)-menthone and other hindered cyclic ketones with aromatic aldehydes under highly basic conditions using a polar aprotic solvent and a strong base (alkali metal hydroxide or an alkoxide) is described and discussed.

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Cited by 34 publications
(21 citation statements)
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“…A plausible explanation of the phenomenon can be the following: Sucrose first undergoes dehydration reaction resulting HMF (5-(hydroxymethyl)-2-furaldehyde) which then take part in polymerization and aldol condensation reactions [32,33,42]. It is reported that aldol reaction of cyclic and aromatic ketones/aldehydes are more favorable under alkaline conditions [43]. Thus, this may lead to faster accumulation of polymerized species which eventually results rapid nucleation.…”
Section: The Effect Of Phmentioning
confidence: 99%
“…A plausible explanation of the phenomenon can be the following: Sucrose first undergoes dehydration reaction resulting HMF (5-(hydroxymethyl)-2-furaldehyde) which then take part in polymerization and aldol condensation reactions [32,33,42]. It is reported that aldol reaction of cyclic and aromatic ketones/aldehydes are more favorable under alkaline conditions [43]. Thus, this may lead to faster accumulation of polymerized species which eventually results rapid nucleation.…”
Section: The Effect Of Phmentioning
confidence: 99%
“…As 4-MBC was no longer commercially available, it was synthesized according to a previously published method [34]. Briefly, camphor (9.13 g, 60 mmol) and 4-methylbenzaldehyde (7.21 g, 60 mmol) were suspended in 100 mL DMSO, and finely ground potassium hydroxide (3.4 g, 60 mmol) was added by degrees.…”
Section: Synthesis Of 4-methylbenzylidene Camphor (4-mbc)mentioning
confidence: 99%
“…Results on the research of the absolute and relative configuration of compounds of the 1 series are in details reported in paper. 11 In conclusion, the reaction of enolate carbanion of 2 (4 bromobenzylidene) p menthan 3 one with ethyl bromoacetate selectively proceeds as the О alkylation. We failed in finding the literature examples of alkylation of 2 arylidenecyclohexanones with haloacetic acid esters.…”
mentioning
confidence: 88%
“…Br (1) C (11) endo and exocyclic double bonds is slightly disturbed (torsion angle С(2)-С(1)-С(6)-С (7) is -162.8(2)°). Bromophenyl substituent is in ар conformation relatively to the С(1)-С (6) There is no reason for the change of the С(5) chiral center configuration during the transformations described.…”
mentioning
confidence: 99%