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These compounds are important in the synthesis of heterocyclic compounds. The analogous 1,4-addition of an aldehyde to an enone is called the Stetter reaction . In biochemistry , the coenzyme thiamine is responsible for biosynthesis of acyloin-like compounds utilizing the benzoin addition.
Benzoin also sees wide spread use in powder coating formulations, where it acts as a degassing agent during the curing stage. This action prevents surface defects such as 'pinholing'. [9] [10] Benzoin can be used in the preparation of several pharmaceutical drugs including oxaprozin, ditazole, and phenytoin. [11]
Tincture of benzoin is a pungent solution of benzoin resin in ethanol. A similar preparation called Friar's Balsam or Compound Benzoin Tincture contains, in addition, Cape aloes or Barbados aloes and storax resin. [1] [2] Friar's balsam was invented by the English doctor and MP Joshua Ward c. 1760. [3]
The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. [1] While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. [2]
It has become a classic reaction in organic synthesis and has been reviewed many times before. [3] [4] [5] It can be viewed as an intramolecular redox reaction, as one carbon center is oxidized while the other is reduced. Scheme 1. Benzilic acid rearrangement
Benzil is a standard building block in organic synthesis. It condenses with amines to give diketimine ligands. A classic organic reaction of benzil is the benzilic acid rearrangement, in which base catalyses the conversion of benzil to benzilic acid. This reactivity is exploited in the preparation of the drug phenytoin.
Benzoin (resin), a balsamic resin obtained from the bark of several species of trees in the genus Styrax; Benzoin aldolase, an enzyme that catalyzes the chemical reaction benzoin to benzaldehyde; Benzoin condensation, a reaction between two aromatic aldehydes; Benzoin odoriferum or Lindera benzoin, a shrub in the laurel family
Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation. Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic ...
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