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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.
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.
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.
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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.
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 ...
Benzaldehyde (C 6 H 5 CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful. It is a colorless liquid with a characteristic almond -like odor , and is commonly used in cherry -flavored sodas . [ 5 ]
The trans,trans isomer can be prepared in high yield and purity by condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium followed by recrystallization. [ 2 ] This reaction, which proceeds via the intermediacy of benzylideneacetone , is often performed in organic chemistry classes, [ 6 ] and is called Claisen ...