36847-79-7

Upstream product

• 36236-72-3 4-chloromethyl-2-phenyl[1,3]dioxolane 
• 65-85-0 benzoic acid 
• 106-89-8 epichlorohydrin 
• 2463-45-8 4-chloromethyl-[1,3]dioxolan-2-one 
• 100-58-3 phenylmagnesium bromide 
• 98-07-7 Benzotrichlorid 
• 96-24-2 3-monochloro-1,2-propanediol 

Relevant academic research and scientific papers

Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran

Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.

A Modified Synthesis of Oxetan-3-ol

Abstract: A highly regioselective ring opening reaction of terminal epoxides with 2-bromobenzoic acid catalyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in a good yield.

Studies on DMDO-mediated benzylidene acetal oxidation

We have shown that dimethyldioxirane (DMDO) can be used to effect an oxidative partial deprotection of benzylidene acetals derived from both 1,2- and 1,3-diols to afford hydroxy benzoate products. A wide range of functional groups are tolerated, and good to excellent yields are usually observed. The reactions are easy to perform and produce little waste other than acetone.

Oxidative transformation of 1,3-dioxacycloalkanes induced by chlorine dioxide

The products and kinetic regularities of the reactions of 1,3-dioxacycloalkanes with chlorine dioxide were studied. The effects of the nature of solvent and the temperature on the reaction rate were considered and the activation parameters were determined.

SYNTHESIS OF HYDROXYAMINO-SUBSTITUTED ESTERS OF AROMATIC ACIDS FROM THEIR CHLOROHYDRIN DERIVATIVES

The hydroxyamino-substituted esters of benzoic, 2-hydroxybenzoic, and 2-acetoxybenzoic acids were synthesized from their chlorohydrin derivatives and a series of aliphatic, aromatic, and heterocyclic amines.

Reactions of 1,3-dioxolanes with Iodine Monochloride: Formation of Chlorohydrin Esters and Diol Monoesters

2-Mono-substituted 1,3-dioxolanes are oxidised by iodine monochloride to the appropriate 2-substituted 1,3-dioxolan-2-ylium ions, whose stability is dependent upon the presence and nature of substituents on C-4 and C-5.Some dioxolanylium ions are labile and under the reaction conditions afford chlorohydrin esters, with inversion of configuration taking place at the ring carbon attacked by chloride.Others are stable under the reaction conditions and may be converted on aqueous workup to diol monoesters with retention of configuration at C-4 and C-5.The effect of substituents and reaction conditions on these competing reactions are described.The stereo- and regio-chemistry of both hydroxy- and chloro-ester formation was confirmed through NMR studies, which necessitated the prior detailed analysis of the 1H and 13C spectra associated with the acyloxy sidechains of the relevant esters.