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The Baeyer–Drewsen indigo synthesis (1882) is an organic reaction in which indigo is prepared from 2-nitrobenzaldehyde and acetone [1] [2] The reaction was developed by von Baeyer and Viggo Drewsen in 1880 to produce the first synthetic indigo at laboratory scale. This procedure is not used at industrial scale.
Benzylideneacetone can be efficiently prepared by the base-induced condensation of acetone and benzaldehyde: [3]. CH 3 C(O)CH 3 + C 6 H 5 CHO → C 6 H 5 CH=CHC(O)CH 3 + H 2 O. However, the benzylideneacetone formed via this reaction can undergo another Claisen-Schmidt condensation with another molecule of benzaldehyde to form dibenzylideneacetone.
The reaction is named after pinacol (also known as 2,3-dimethyl-2,3-butanediol or tetramethylethylene glycol), which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859
2-Nitrobenzaldehyde is an intermediate in an early route to indigo, a water-insoluble dye commonly used to dye jeans and other fabrics.In the Baeyer-Drewson indigo synthesis, 2-nitrobenzaldehyde condenses with acetone in basic aqueous solution to yield indigo in a one-pot synthesis [9] [10] The method was abandoned in the early part of the 20th century, being replaced by routes from aniline.
In the classic example, benzaldehyde is converted to benzoin (PhCH(OH)C(O)Ph). [3] The benzoin condensation was first reported in 1832 by Justus von Liebig and Friedrich Wöhler during their research on bitter almond oil. [4] The catalytic version of the reaction involving cyanide was developed by Nikolay Zinin in the late 1830s. [5] [6 ...
Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone. [ 6 ] This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of green chemistry in undergraduate education.
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen.