162426-86-0

Basic information

• Product Name: (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol
• Synonyms: (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol
• CAS NO: 162426-86-0
• Molecular Weight: 160.17
• Mol File: 162426-86-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol(162426-86-0)
• EPA Substance Registry System: (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol(162426-86-0)

Safety Data

• Hazardous Substances Data: 162426-86-0(Hazardous Substances Data)

Usage

General Description

(1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol, also known as 8-methoxy-2,6-dioxabicyclo[3.3.0]octane-1,4,5-triol, is a chemical compound with a bicyclic structure. It is a derivative of cyclooctane and contains a methoxy group and three hydroxyl groups. (1R,4S,5R,8R)-8-methoxy-2,6-dioxabicyclo[3.3.0]octanol may have potential applications in the pharmaceutical or agrochemical industries due to its unique structure and potential biological activity. However, further research is needed to fully understand its properties and potential uses.

Upstream product

• 50-70-4 D-sorbitol 
• 616-38-6 carbonic acid dimethyl ester 
• 652-67-5 Isosorbide 
• 1235553-24-8 isosorbide di(methyl carbonate) 
• 67-56-1 methanol 
• 110-71-4 1,2-dimethoxyethane 
• 100-66-3 methoxybenzene 
• 112-49-2 Triethylene glycol dimethyl ether 
• 111-96-6 diethylene glycol dimethyl ether 
• 109-87-5 Dimethoxymethane 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 1609973-55-8 C₂₈H₃₉N₃O₈S 
• 1609973-53-6 C₂₉H₄₀N₂O₉S 
• 1609973-50-3 C₁₄H₁₅NO₈ 

Relevant articles and documents

Dimethyl isosorbideviaorganocatalystN-methyl pyrrolidine: scaling up, purification and concurrent reaction pathways

Dimethyl isosorbide (DMI) is a well-known bio-based green replacement for conventional dipolar solvents such as dimethyl sulfoxide and dimethylformamide. The synthesis of DMI mainly relies on the etherification of the bio-based platform chemical isosorbide in the presence of basic or acid catalysts and by employing different alkylating agents. Among them, dimethyl carbonate (DMC) is considered one of the most promising for its good biodegradability and low toxicity. In this work, we report on a comprehensive investigation on high yielding methylation of isosorbideviaDMC chemistry promoted by nitrogen organocatalystN-methyl pyrrolidine (NMPy). Reaction conditions were optimized and then efficiently applied for the methylation of isosorbide epimers, isoidide and isomannide, and for some preliminary scale-up tests (up to 10 grams of isosorbide). The purification of DMI from the reaction mixture was achieved by both column chromatography and distillation at reduced pressure. NMPy demonstrated to be an excellent catalyst also for the one-pot conversion ofd-sorbitol into DMI. Furthermore, for the first time, all seven methyl and methoxycarbonyl intermediates observed in the etherification of isosorbide were synthetised, isolated and fully characterised. This has provided an insight on the concurrent reaction pathways leading to DMI and on the role played by NMPy in the methylation of isosorbide. Finally, the reaction mechanisms for the methylation, methoxycarbonylation and decarboxylation promoted by NMPy partaking in the conversion of isosorbide into DMIviaDMC chemistry have been proposed.

Method for preparing dialkyloxydianhyrohexitol by etherification of dianhydrohexitol using a light alcohol, in the presence of an acidic catalyst

A method for preparing a dialkyloxydianhyrohexitol (dimethylisosorbide) composition by etherification of dianhydrohexitol (isosorbide). The aim is to achieve a “clean” method that avoids the use of a methylation agent such as dimethyl sulfate or methyl chloride, which generates stoechiometric quantities of salts, or expensive dialkyl-carbonates, wherein only one of the two methyl groups participates in the preparation of mixed isosorbide ethers. The method involves using at least one O-alkylation agent and a catalyst including an acid or an acid salt, preferably a catalyst having Lewis or Br?nsted acid properties. A device for carrying out the method wherein the device includes a vaporization oven and a reaction oven is also described.

Green synthesis of dimethyl isosorbide

A green synthetic approach for dimethyl isosorbide (DMI) with dimethylcarbonate (DMC) in the presence of a base is reported. The easy methylation of isosorbide may be due to its unique structure (which enhances the nucleophilicity of the hydroxyl groups), and to the effect of the hydrogen bonding which increases the reactivity of the molecule towards DMC.