This article is about synthesis of Benzoin. For other uses, see Benzoin (disambiguation).
The benzoin addition is an addition reaction involving two aldehydes. The reaction generally occurs between aromatic aldehydes or glyoxals,[1][2] and results in formation of an acyloin. In the classic example, benzaldehyde is converted to benzoin.[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]
^Enders, Dieter; Niemeier, Oliver; Henseler, Alexander (2007). "Organocatalysis by N-Heterocyclic Carbenes". Chemical Reviews. 107 (12): 5606–5655. doi:10.1021/cr068372z. PMID 17956132.
^Roger Adams; C. S. Marvel (1921). "Benzoin". Organic Syntheses. 1: 33. doi:10.15227/orgsyn.001.0033.
^F. Wöhler, J. Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure" [Studies on the radicals of benzoic acid]. Annalen der Pharmacie (in German). 3 (3): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
^N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe" [Contributions to the knowledge of some compounds from the benzoyl series]. Annalen der Pharmacie (in German). 31 (3): 329–332. doi:10.1002/jlac.18390310312. Archived from the original on 2022-07-09. Retrieved 2020-09-11.
^N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls" [Study of some decomposition products of bitter almond oil]. Annalen der Pharmacie (in German). 34 (2): 186–192. doi:10.1002/jlac.18400340205. Archived from the original on 2022-07-09. Retrieved 2019-06-28.
and 27 Related for: Benzoin condensation information
acyloin. In the classic example, benzaldehyde is converted to benzoin. The benzoincondensation was first reported in 1832 by Justus von Liebig and Friedrich...
chemical reaction benzoin to benzaldehyde Benzoincondensation, a reaction between two aromatic aldehydes Benzoin odoriferum or Lindera benzoin, a shrub in...
mechanism; for example, see the illustration of the mechanism for benzoincondensation in the following examples section. A reaction mechanism must also...
self-reaction of formaldehyde in hydroxide to form aldose sugars Benzoincondensation - self-reaction of aldehydes to give α-hydroxy ketones Meerwein–Ponndorf–Verley...
nucleophilic catalyst. While the related 1,2-addition reaction, the benzoincondensation, was known since the 1830s, the Stetter reaction was not reported...
trimethylsilyl cyanide. With aromatic aldehydes such as benzaldehyde, the benzoincondensation is a competing reaction. The reaction is used in carbohydrate chemistry...
cyanide is a key catalyst in the benzoincondensation, a classical example of polarity inversion. The net result of the benzoin reaction is that a bond has...
formaldehyde. glycolonitrile acetone cyanohydrin mandelonitrile Halohydrin Benzoincondensation David T. Mowry (1948). "The Preparation of Nitriles". Chem. Rev....
cyanohydrin or aldehyde-dithiane umpolung chemistry, as well as benzoincondensation). This anion attacks S1 of an oxidized lipoate species that is attached...
compound with formula C10H8O4. It can be produced from furfural by a benzoincondensation reaction catalyzed by cyanide ions. Furoin synthesis from furfural...
synthesis of acyloins. The acyloin condensation is a reductive coupling of esters The benzoincondensation is condensation reaction between aldehydes catalyzed...
structure first made an appearance in the reaction mechanism for the benzoincondensation as correctly proposed by Clarke and Arthur Lapworth in 1907. In 1904...
organic chemistry. His proposal for the reaction mechanism for the benzoincondensation is the basis for our modern-day understanding of organic chemistry...
NHCs are known to catalyse a number transformations such as the Benzoincondensation and the OTHO reaction. Recognizing that approximately 50% of commercial...
derivative of vitamin B1 (thiamine), was the catalyst involved in the benzoincondensation that yields furoin from furfural. In this cycle, the vitamin's thiazolium...
Thiazolium salts are catalysts in the Stetter reaction and the Benzoincondensation. Deprotonation of N-alkyl thiazolium salts give the free carbenes...
alcoholic potassium cyanide can be used to catalyze the condensation of benzaldehyde to benzoin. Benzaldehyde undergoes disproportionation upon treatment...
Justus Liebig in Giessen, where he finished his research on the benzoincondensation, which was discovered by Liebig several years before. He presented...
with 1,3-diphenylacetone in an aldol condensation to give tetraphenylcyclopentadienone. Benzil is prepared from benzoin, for example with copper(II) acetate:...
classified as a carcinogen. The word "benzene" derives from "gum benzoin" (benzoin resin), an aromatic resin known since ancient times in Southeast Asia...
the Ming Dynasty Taoist Manual, avoid the use of sandalwood (as well as benzoin resin and frankincense) as incense in worship. In Korean Shamanism, sandalwood...
scent that is warm, musky, rich and honey-like, and also somewhat earthy. Benzoin is usually part of the recipe. Vanilla and cloves are sometimes used to...
from the original on June 25, 2014. Retrieved January 16, 2015. "Lindera benzoin (spicebush)". Monticello.org. Retrieved January 16, 2015. "History and...
"Photochemical Studies of the Porphyrins. III. Photoreduction of a Porphyrin by Benzoin" Journal of Chemical Physics, volume 23, issue 6, pages 1068–. doi:10.1063/1...
diethyl oxalate and 3,3-dimethylpentanoic acid, which reacted by Claisen condensation to yield diketocamphoric acid. Methylation with methyl iodide and a complicated...
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