Untersuchungen in der Kumarinreihe. 2. Synthese einiger Kumarinaldehyde; mit Bemerkungen über die katalytische Hydrierung der Säurechloride

Boehm, Theodor; Schumann, G.; Hansen, Hanspeter

doi:10.1002/ardp.19332710808

Cited by 17 publications

(1 citation statement)

References 5 publications

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“…In many reductions, however, it is not necessary to use a regulator and in some reductions the use of poison appears to be definitely disadvantageous. The decisive factor in the acid chloride reduction is the temperature [12]. If the temperature is kept near the lowest point at which hydrogen chloride is evolved, the aldehydes are obtained in optimum yields.…”

Section: Discussionmentioning

confidence: 99%

The Use of Rosenmund Reduction in Organic Synthesis

Banerjee

2023

OMCIJ

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The diverse uses of commercially available Palladium (Pd) on barium sulfate, known as Rosenmund catalyst are described. Hydrogenation of acid chloride to aldehyde with poisoned palladium catalyst (Pd-BaSO4) is known as Rosenmund reduction. The Rosenmund reduction has also been used in the conversion of alkynes to cis-alkenes and hydrogenolysis of various functional groups. The regioselective opening of 1,2-disubstituted epoxide has been recorded with Rosenmund reduction.

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Section: Discussionmentioning

confidence: 99%

The Use of Rosenmund Reduction in Organic Synthesis

Banerjee

2023

OMCIJ

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The Rosenmund Reduction of Acid Chlorides to Aldehydes

Mosettig

Mozingo

2011

Organic Reactions

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In the synthesis of complex molecules, particularly in connection with natural products, it is occasionally desirable to prepare an aldehyde when the readily available starting material is the corresponding acid. The Rosenmund reduction is probably the most useful method for application to a large number of aldehdyes of varied types. The Rosenmund reduction consists in the selective hydrogenation of an acid chloride in the presence of a suitable catalyst, usually supported palladium to the corresponding aldehyde.

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TheKnoevenagel Condensation

Jones

2011

Organic Reactions

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Knoevenagel's first papers in this field were concerned with the condensation of formaldehyde with diethyl malonate and with ethyl benzoylacetate. The catalyst was ethylamine. A number of other aldehydes were reported to condense similarly with diethyl malonate, ethyl benzoylacetate, ethyl benzoylpyruvate, and acetylacetone under the influence of various primary and secondary amines. In 1896, Knoevenagel reported benzaldehyde with ethyl aceoacetate condensed at room temperature in the presence of piperdine to give a bis compound, but that when the reaction was run in a freezing mixture, the product was acetoacetate. For the purposes of this chapter, the Knoevenagel condensation is defined as the reaction between an aldehyde or ketone or any compound having an active methylene group, brought about by an organic base or ammonia and their salts.

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Untersuchungen in der Kumarinreihe. 2. Synthese einiger Kumarinaldehyde; mit Bemerkungen über die katalytische Hydrierung der Säurechloride

Cited by 17 publications

References 5 publications

The Use of Rosenmund Reduction in Organic Synthesis

The Use of Rosenmund Reduction in Organic Synthesis

The Rosenmund Reduction of Acid Chlorides to Aldehydes

TheKnoevenagel Condensation

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