59517-16-7

Upstream product

• 63087-43-4 2-Chloro-4,5-dimethyl-1,3,2-dioxarsol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 513-85-9 2.3-butanediol 
• 114431-75-3 (2RS,3RS)-2--1-methylpropyl benzoate 
• 4359-31-3 4,5-dimethyl-2-phenyl-[1,3]dioxolane 
• 82240-83-3 2-chloro-4,5-dimethyl-1,3,2-dioxastibolane 

Downstream Products

• 5320-92-3 (2RS,3RS)-butane-2,3-diol dibenzoate 
• 1418123-72-4 C₁₅H₂₀O₄ 
• 1418123-73-5 C₁₅H₂₀O₄ 

Relevant academic research and scientific papers

A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating

A convenient method for the selective protection of primary hydroxyl groups in 1,n diols is described. The use of microwave heating is shown to be advantageous.

The Phenyldimethylsilyl Group as a Masked Hydroxy Group

A phenyldimethylsilyl group attached to carbon can be converted into hydroxy group 1->5, with retention of configuration at the migrating carbon, by any of three main methods.The first involves protodesilylation, to remove the phenyl ring from the silicon atom, followed by oxidation of the resulting functionalized silicon atom using peracid or hydrogen peroxide.The second uses mercuric acetate for the same purpose, and can be combined in one pot with the oxidative step using peracetic acid.This method has a variant in which the mercuric ion is combined with palladium(II) acetate, both in less than stoichiometric amounts.The third uses bromine, which can also be used in one pot in conjuction with peracetic acid.In this method, but not in the method based on mercuric acetate, the peracetic acid may be buffered with sodium acetate.The method using bromine as the electrophile for removing the benzene ring has a more agreeable variant in which it is administered in the form of potassium bromide, which is oxidised to bromine by the peracetic acid.The scope and limitations of each of these methods are reported with a range of examples possessing between them many of the common functional groups.Simple benzene rings, alcohols, ethers, esters, amides and nitriles are compatible with all three methods, and ketones do not undergo Baeyer-Villiger reaction under any of the conditions.Amines, however, are oxidised to amine oxides.Ketones may be brominated in the third of the three main species.The absence of acid in the third method makes it especially valuable when the phenyldimethylsilyl group has a neighbouring nucleofugal group such as hydroxy or acetoxy.Carbon-carbon double bonds are incompatible with the methods, except for terminal monosubstituted double bonds, which can survive the conditions used in the first of the three methods.

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.

A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP

A phenyldimethylsilyl group attached to carbon can be converted into a hydroxyl group using either bromine or mercuric ion in an acetic acid solution of peracetic acid.

Studies on the Synthesis of Heterocyclic Compounds. VII. Action of Acyl Halides on Heterocyclic Compounds Containing the O-M-O (M = P, As, Sb) Bond in the Ring

The action of acyl halides on heterocyclic compounds of five-membered rings containing an O-M-O (M = P, As, Sb) linkage is described.The reactions were either carried out in the presence of a solvent (benzene or toluene) or by direct heating of the reagent with the substrate.In the case of arsole, stibole and stannole derivatives, the cleavage of O-M bond and the formation of the respective mono- and diesters were always obtained, while with the phospholes, no cleavage of the compounds was observed.The products IIa-c (M = Sb) have been obtained in excellent yields starting from VIa-c and antimony trichloride.The structure of the compounds which were prepared was determined by analytical and spectroscopic methods and also by comparations with authentic samples where possible.

Reaction of 1,3-dioxolans with Iodine Monochloride: the Scope and Mechanism of Formation of 1,3-dioxolan-2-ylium Dichloroiodates(I)

Treatment of a series of 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolanes with iodine monochloride afforded the appropriate 2-substituted-4,4,5,5-tetramethyl-1,3-dioxolan-2-ylium dichloroiodate(I) salts in excellent yields.In contrast to the stable 2-aryl-substituted salts, the 2-alkyl and unsubstituted derivatives were relatively labile.While 2-phenyl-1,3-dioxolan and 2-phenyl-1,3-dioxan afforded low yields of unstable salts,crystalline products could not be isolated from 4,5-disubstituted dioxolans.The reaction was inhibited by electron-withdrawing 4- and 5-substituents.From a study of the effects of photolysis and added iodine, the mechanism is proposed to involve a hydride ion transfer.Possible reasons for the formation of dichloroiodate(I) rather then monohalide salts, are outlined.The stability of the 2-aryl-substituted salts is dicussed in terms of charge distribution in the cation and possible aryl-anion interactions.

METALLOID DERIVATIVES FOR SYNTHESIS: MONODERIVATIZATION OF SYMMETRIC DIOLS

The monoderivatization of symmetric diols by condensation of their stannoxanes with activated halides is described.