53226-58-7

Upstream product

• 36967-85-8 benzoyl triflate 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 931-17-9 1,2-Cyclohexanediol 
• 98-88-4 benzoyl chloride 
• 286-20-4 cyclohexane-1,2-epoxide 
• 28141-32-4 2-Iodo-cyclohexanol 
• 64548-92-1 N-benzoyl-4-(N,N-dimethylamino)pyridinium chloride 
• 57701-19-6 trans-1,2-Bis(thiobenzoyloxy)cyclohexan 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 108592-06-9 (+/-)-trans-4,5-bis-benzoyloxy-cyclohexene 
• 110-82-7 cyclohexane 
• 532-31-0 silver benzoate 
• 87-66-1 2-hydroxyresorcinol 

Relevant academic research and scientific papers

N-benzoyl-4-(dimethylamino)pyridinium chloride: Isolation and use for the direct benzoylation of alcohols

A simple method for the formation and isolation of N-benzoyl-4- (dimethylamino)pyridinium chloride is described. This reagent can be employed directly for the benzoylation of secondary and tertiary alcohols.

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% H2O2 in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.

Reduction of diesters of 1,2-diols. Regioselective C-O bond cleavage of the anionic forms

The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N,N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC(O)Ar bonds and the RO-C(O)Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano- and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4′-dicyanobenzil from four different p-cyanobenzoate diesters.

Regioselective benzoylation of 6-O-protected and 4,6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1,2-diamines

Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at - 60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends

Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds

A new facile method for monoacylation of diols has been developed. A variety of cyclic and acyclic diols, in particular 1,2-diols, were selectively monobenzoylated in good yields by the reaction with benzoyl chloride in the presence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully applied to a kinetic resolution of racemic 1-phenyl-1,2- ethanediol using a chiral organotin catalyst. The ee was dependent on the kind of base, water as an additive, and the reaction temperature.

Remarkably fast acylation of alcohols with benzoyl chloride promoted by TMEDA

Reaction of alcohols with benzoyl chloride in the presence of TMEDA at - 78°C resulted in very fast acylation to afford the corresponding benzoates in excellent yields.

Benzoyl Trifluoromethanesulfonate. A Mild Reagent for the Benzoylation of Sterically Hindered Hydroxyls

Benzoyl trifluoromethanesulfonate (BzOTf) is a highly efficient reagent for the benzoylation of a variety of alcohols under mild conditions.These include hindered secondary and tertiary hydroxyls, phenols, and α-glycols.Sensitive functionality is stable when the reaction is performed in the presence of pyridine.Several unique rearrangements of Lewis acidsensitive compounds were also effected.

STUDIES ON THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS. IX. SEPARATION OF DIASTEREOMERIC DIOL COMPOUNDS

The separation of diastereomeric diols by transformation into the corresponding dioxastannolanes was carried out.The products are solid, stable and easily separable by fractional crystallization.By reaction of acids (or acyl halides) with the stannolanes the corresponding diols (or esters) were obtained in a high degree of purity.The structures of the compounds prepared were assigned on the basis of their analytical, physical and spectral data.

Benzoyl Trifluoromethanesulphonate. A Highly Efficient Benzoylating Agent for Sterically Hindered Hydroxyl Groups

Reactions of benzoyl trifluoromethanesulphonate (BzOTf) with a variety of alcohols, including some with sterically hindered secondary and tertiary hydroxy groups, with phenolic compounds, and with 1,2-diols at low temperatures provide the corresponding benzoates in high yield.

Conversion of Thiocarbonyl Compounds into their Corresponding Oxo-derivatives using Benzeneseleninic Anhydride

A series of thiocarbonyl compounds including xanthates, thioesters, thioureas, thiocarbonates, and thiones have been converted into their oxo-analogues by treatment with benzeneseleninic anhydride in tetrahydrofuran at room temperature.Except for readily enolised thiones where further oxidation can take place, the method works well and compares favourably with other literature procedures.One example of a selenocarbonyl ester was likewise converted efficiently into the corresponding ester.