134070-80-7

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 67-63-0 isopropyl alcohol 
• 286-20-4 cyclohexene oxide 
• 110-83-8 cyclohexene 
• 64672-72-6 2-(dimethoxymethylidene)propanedinitrile 
• 24796-87-0 2-bromo-cyclohexanol 

Downstream Products

• 134070-89-6 Butyric acid (1S,2S)-2-isopropoxy-cyclohexyl ester 
• 134108-80-8 Butyric acid (1S,2S)-2-isopropoxy-cyclohexyl ester 
• 134108-70-6 (1R,2R)-2-Isopropoxy-cyclohexanol 

Relevant academic research and scientific papers

Highly efficient, regio- and stereoselective alcoholysis of epoxides catalyzed with iron(III) chloride

An efficient, catalytic, simple and mild method for the conversion of epoxides into their corresponding β-alkoxy alcohols was performed in primary, secondary and tertiary alcohols and in the presence of catalytic amounts of ferric chloride. The β-alkoxy alcohols were obtained with high stereo- and regioselectivity and in good to excellent yields.

Cross-linked poly(N-vinylpyrrolidone)-titanium tetrachloride complex: A novel stable solid TiCl4 equivalent as a recyclable polymeric Lewis acid catalyst for regioselective ring-opening alcoholysis of epoxides

Cross-linked poly(N-vinylpyrrolidone) resin beads were prepared as macromolecular ligand precursors by suspension copolymerization of N-vinyl-2-pyrrolidone and N,N′-methylenebisacrylamide (MBA) as a crosslinking agent in water. Subsequently, the resulting polymer carrier precursor was readily combined with titanium tetrachloride to form a stable polymeric coordination complex (PNVP/TiCl4), and this novel stable TiCl4 equivalent evaluated as a heterogeneous and reusable solid Lewis acid catalyst for the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols to prepare β-alkoxy alcohols in excellent yields without generating any waste. The MBA-cross-linked PNVP and resultant catalyst were characterized by Fourier transform infrared spectroscopy (FT–IR), field-emission scanning electron microscope (FE–SEM), energy dispersive X-ray (EDX), inductively coupled plasma (ICP), and thermogravimetric analysis (TGA) techniques. Moreover, the catalyst is very stable, easily separated, and reused at least five times without significant loss of activity. In terms of scope, yields, the amount of catalyst used, and reaction time, the PNVP-TiCl4 complex catalyst is an improvement over previously reported heterogeneous catalysts for ring opening of epoxides methods. Further, the experimental outcome revealed that using the copolymer beads as carriers with a high percentage of crosslinking and the high mesh size leads had an adverse effect on the reaction rate.

MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides

A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.

Synthesis and structure of an air-stable bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate and its application in catalytic epoxide ring-opening reactions

An air-stable mononuclear complex of bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate was successfully synthesized by treating C6F5SO3Ag with [(CH3)5Cp]2ZrCl2, which showed the cationic uninuclear structure of [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN (1) confirmed by the X-ray analysis. Complex 1 was also characterized by other techniques and found to have the good nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. Moreover, the complex showed high catalytic activity and recyclability in catalytic epoxide ring-opening reactions by amines or alcohols. This catalytic system affords a simple and efficient approach for synthesis of β-amino alcohols or β-alkoxy alcohols.

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.

CuO/SiO2: A simple and efficient solid acid catalyst for epoxide ring opening

A cheap, non toxic, easy to prepare and easy to use supported CuO material has shown to be a very effective catalyst for the alcoholysis of epoxides giving β-alkoxyalcohols in very good yield without generating any waste. The catalyst is heterogeneous in nature and can be reused without any reactivation treatment. The Royal Society of Chemistry.

Synthesis, structures, and heterogeneous catalytic applications of {Co 3+-Eu3+} and {Co3+-Tb3+} heterodimetallic coordination polymers

Two {Co3+-Eu3+} and {Co3+-Tb3+} heterodimetallic coordination polymers have been synthesized by using a Co 3+-based coordination complex as the building block. Structural studies show that the lanthanide atoms are coordinated to the cobalt complex through Oamide groups. This results in the generation of a one-dimensional zigzag coordination polymer. These coordination polymers have been shown to catalyze the ring-opening reactions of the epoxides with anilines and alcohols under heterogeneous and solvent-free conditions. Interestingly, a perfect regioselectivity was observed in the aminolysis and alcoholysis reaction of styrene oxide. Two {Co3+-Eu3+} and {Co 3+-Tb3+} zigzag coordination polymers have been synthesized by using a Co3+-based coordination complex. These coordination polymers have been shown to catalyze the ring-opening reactions of epoxides with anilines and alcohols under heterogeneous and solvent-free conditions.

Epoxide ring-opening and Meinwald rearrangement reactions of epoxides catalyzed by mesoporous aluminosilicates

Mesoporous aluminosilicates efficiently catalyze the ring-opening of epoxides to produce β-alkoxyalcohols in high yields under extremely mild reaction conditions. These materials also catalyze the corresponding Meinwald rearrangement in non-nucleophilic solvents to give aldehydes which can be trapped in situ to provide the corresponding acetals in an efficient tandem process. The Royal Society of Chemistry 2009.

Rapid ring-opening reactions of epoxides using microwave irradiation

Copper tetrafluoroborate catalyzes the ring-opening of epoxides with primary, secondary, and tertiary alcohols in short reaction times under microwave irradiation to give β-alkoxyalcohol products in excellent yields. Copyright Taylor & Francis Group, LLC.

Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)

Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.