Benzoyl carbinol

Acyloins have also been employed extensively as starting materials for the synthesis of imidazoles, usually in the presence of added aldehyde (or acid) and using ammoniacal cupric acetate to oxidize the acyloin to the corresponding a-dicarbonyl compound.24 Alicyclic and aromatic ketols and ketol acetates in an alcoholic solution of cupric acetate and ammonia undergo ring closure to the corresponding 2-imidazoyl ketones. Hence, benzoyl carbinol refluxed for 1 hour in... 

Methyl groups in pyridopyrazines (64IMC240) and pyridopyrazinones (71TH21500) are oxidized to carboxylic acids with potassium permanganate. Aryl carbinol substituents are also very readily oxidized to benzoyl derivatives in alkaline conditions (76CPB238). Bromina-tion of 2,3-dimethylpyrido[3,4-f ]pyridazine gives the 2,3-bisbromomethyl derivative, whilst... 

The lithium cnolate generated by deprotonation of 2-/m-butyl-6-methyl-l,3-dioxan-4-onc, readily available from polyhydroxybutyric acid (PHB), predominantly affords the diastereo-mers 7 when reacted with aldehydes. The diastereomeric ratios of aldol adducts 7/8, produced by reactions with aliphatic aldehydes, range from 87.5 12.5 to >99 1. Pure diastereoiners7are obtained by recrystallization in 25-74% yield116-118. Only marginal diastereoselectivities with respect to the carbinol center are obtained with aromatic aldehydes111-119. Benzoylation of the dioxanones 7, followed by reduction with lithium aluminum hydride, affords enan-tiomerically and diastereomerically pure triols 9 in >85% yield 11. ... 

Synonyms AI3-01680 Benzal alcohol Benzene carbinol Benzene methanol Benzoyl alcohol Benzylicum BRN 0878307 Caswell No. 081F CCRIS 2081 EINECS 202-859-9 EPA pesticide chemical code 009502 Elydroxymethylbenzene a-Elydroxytoluene NC1-C06111 NSC 8044 Phenol carbinol Phenyl carbinol Phenyl methanol Phenyl methyl alcohol a-Toluenol UN 2810. 

The anions of Reissert compounds 19 and 20 undergo reaction with aldehydes to form esters of secondary alcohols containing the 2-quinolyl or 1-isoquinolyl group bonded to the carbinol carbon atom. Thus benzaldehyde, l-benzoyl-l,2-dihydroquinaldonitrile (7), and phenyllithium in ether-dioxan at — 10° gave 29, and benzaldehyde, 2-benzoyl-l,2-dihydroisoquinaldonitrile (8), and phenyllithium in ether-dioxan at —10° (or sodium hydride in refluxing... 

Two other novel transformations are possible with this reagent. Methyl decanoate (8) undergoes twofold addition with the reagent at -25° to give bisphenylthiomethyl-carbinol (9, 73% yield). Benzoylation and reduction (Li/NHj) effects both vicinal elimination and allylic cleavage to give 2-methyl-1-undecene (10). 

The reagent formed by combining PhsP with benzoyl peroxide (BPO) reacts with alcohols to give benzoates in moderate to good yields. The reaction proceeds with essentially complete inversion of the configuration at the secondary carbinol stereocenters. It is noteworthy that 1,2-diols are benzoylated at the secondary hydroxy group in preference to the primary one (Scheme 46). The product ratio is practically the same as that obtained by the DEAD-PhsP procedure. Therefore, as far as benzoylation is concerned, the BPO-PhsP procedure seems attractive because the removal of hydrazine dicarboxylate from the desired product is sometimes troublesome in the DEAD-PhsP procedure. 

Synonyms Benzene carbinol Benzene methanol Benzoyl alcohol Phenyl carbinol Phenyl methanol Hydroxymethyl benzene Hydroxy toluene... 

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