869-50-1

Usage

InChI:InChI=1/C7H11ClO4/c1-5(9)11-4-7(3-8)12-6(2)10/h7H,3-4H2,1-2H3

Upstream product

• 102-76-1 triacetylglycerol 
• 556-52-5 oxiranyl-methanol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 64-19-7 acetic acid 
• 56-81-5 glycerol 
• 24573-30-6 3-chloro-2-hydroxy-1-propyl acetate 
• 75-05-8 acetonitrile 
• 108-22-5 Isopropenyl acetate 
• 108-05-4 vinyl acetate 
• 93713-40-7 Glycerin-monoacetat 
• 2156-73-2 2-acetoxy-2-methylbutyryl chloride 
• 106-89-8 epichlorohydrin 

Downstream Products

• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 52829-30-8 7-chloro-1-(2,3-dihydroxy-propyl)-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 

Relevant academic research and scientific papers

Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation

The well-known epoxide-Ritter reaction generally affords oxazolines with poor to average regioselectivity. Herein, a mechanism-based study of the less known diol-Ritter reaction has provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis acid-catalyzed monoesterification. When treated with a stoichiometric Lewis acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation is irreversible and appears to occur through disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyses and chiral chromatography, respectively. The direct access to chiral vic-amidoesters is especially practical with regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial family.

A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3

SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.

Heterogeneous acidic and eco-friendly reagents for mild and convenient conversion of epoxides to 1,2-diacetates

A highly regioselective ring-opening of epoxides with acetic anhydride in the presence of hydrated disodium hydrogen phosphate and sodium hydrogen sulfate as efficient and eco-friendly reagents is described. The reactions are clean and lead to 1,2-diacetates in high to excellent yields.

Solventless acetylation of alcohols and phenols catalyzed by supported iron oxide nanoparticles

Supported iron oxide nanoparticles on silicate catalysts were found to be efficient and easily recoverable materials in the acetylation of alcohols and phenols to their corresponding acetyl compounds using acetic anhydride under mild and solvent-less conditions. The supported iron oxide nanoparticles could be easily recovered from the reaction mixture and reused ten times without any loss in activity.

One-pot catalytic conversion of epoxides to 1,2-diacetates with hydride transferring agents in acetic anhydride

Direct transformation of structurally different epoxides to the corresponding 1,2-diacetates was studied with catalytic amounts of NaBH 4, LiAlH4, CaH2, and NaH. The reactions were carried out in refluxing acetic anhydride within 1.5-2.5h to give vic-diacetates in good to excellent yields. Conversion of R-(+)-styrene oxide to S-(+)-1,2-diacetoxy-1-phenylethane was carried out with good yield and stereospecificity with the NaBH4/Ac2O system at 0°C.

Mild organic ammonium tribromide-mediated regioselective ring opening of epoxides with alcohols, water, acetic anhydride, and amines under solvent-free reaction conditions

Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.

A green protocol for catalytic conversion of epoxides to 1,2-diacetoxy esters with phosphomolybdic acid alone or its supported on silica gel

Catalytic conversion of structurally different epoxides to the corresponding 1,2-diacetoxy esters was carried out readily with phosphomolybdic acid alone or its supported on SiO2. The reactions were carried out under solvolytic or solvent free conditions within 5-15 min at room temperature. The product 1,2-diacetates were obtained in high to excellent yields. Supporting of phosphomolybdic acid on SiO2 showed the better catalytic activity than Al2O3. Conversion of optically pure R-(+)-styrene oxide to S-(+)-1,2-diacetoxy-1-phenylethane was carried with phosphomolybdic acid in high yield and stereospecificity.

A heterogeneous cobalt(II) Salen complex as an efficient and reusable catalyst for acetylation of alcohols and phenols

Acetylation of various alcohols and phenols was performed successfully using an immobilized cobalt(II) catalyst in high yield. The catalyst shows high thermal stability and was also recovered and reused at least 10 times without any considerable loss of activity.

Alumina-supported molybdenum (VI) oxide: An efficient and recyclable heterogeneous catalyst for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols under solvent-free conditions

An efficient and simple protocol for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols using 16wt% MoO3 supported on alumina as a recyclable catalyst is described. Copyright

A mild, rapid and highly regioselective ring-opening of epoxides and aziridines with acetic anhydride under solvent-free conditions using ammonium-12-molybdophosphate

A highly regioselective ring opening of epoxides and aziridines can be carried out efficiently with acetic anhydride to form the acetates of the corresponding 1,2-diols and 2-amino-alcohols, respectively, using ammonium-12-molybdophosphate (AMP) as a heterogeneous catalyst, at room temperature, in the absence of solvent.