29839-75-6

Usage

Uses

Used in Industrial Applications:
2,2,3,5,5-pentamethyltetrahydrofuran-3-ol is used as a solvent for various industrial applications due to its stability, high boiling point, and low vapor pressure. These properties make it an ideal choice for processes that require a non-volatile and stable solvent.
Used in Green Chemistry Practices:
2,2,3,5,5-pentamethyltetrahydrofuran-3-ol is used as a solvent in green chemistry practices because of its biodegradable nature and relatively low environmental impact. This makes it a favorable choice for chemists and industries that prioritize sustainability and eco-friendliness in their processes.

Upstream product

• 5455-94-7 2,2,5,5-tetramethyltetrahydro-3-oxofuran 
• 75-16-1 methylmagnesium bromide 
• 76158-32-2 α,α,2,3,3-pentamethyl oxirane-ethanol 
• 142-30-3 2,5-dihydroxy-2,5-dimethyl-3-hexyne 
• 53256-16-9 trimethyl-2,4,5 hexene-4 ol-2 
• 1195-55-7 2,4-dihydroxy-2,4-dimethylpentanoic acid γ-lactone 
• 917-64-6 methyl magnesium iodide 
• 823192-27-4 2,3,5-trimethyl-2,3,5-hexanetriol 
• 76158-32-2 2-Methyl-1-(2,3,3-trimethyl-oxiranyl)-propan-2-ol 

Relevant academic research and scientific papers

Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100percent sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-2,3,5,5-tetramethylfuran-2,3-diol (11), 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (18), 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25).In 96percent sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, methyl migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation.In ca. 100percent sulfuric acid or hot polyphosphoric acid further methyl migrations can occur to give 23 and 25.

TRANSPOSITION DES OXIRANNES-ETHANOLS PAR L'INTERMEDIAIRE D'ALCOXYETAINS

Oxiraneethoxytributyltins prepared from the corresponding oxiraneethanols, on heating at 200 deg C gave, after demetalation with isophthalic acid, 2-oxetanemethanols and/or 3-oxolanols.As appears from about thirty rearrangements the choice between oxetane and oxolane formation is dependent on: (1) the relative degree of substitution of the oxirane ring; cyclization occuring predominantly at the more substituted carbon; and (2) the configuration of the oxirane ring, when both its ends are equally substituted; cis form being more suitable for genaration of the smaller ring.The reaction is shown to proceed with inversion of configuration at the site of oxygen attack.The results of attempts to perform the rearrangement in dilute-phase or throught alkaline metal alkoxides in various media support the conclusion that there is a large contribution by electrophilic assistance to the oxirane ring opening.Such assistance can be efficiently provided by a tin atom in a push-pull mechanism which accomodates all the facts.The present method of oxiraneethanol rearrangement may offer a convenient route to functional oxetanes.

TRANSPOSITION DES OXIRANNES-ETHANOLS PAR L'INTERMEDIAIRE D'ALCOXYETAINS. INFLUENCE DE LA CONFIGURATION DE L'OXIRANNE

The transposition of oxirane-ethanols, through alkoxytin compounds, into oxetane-2-methanols and/or oxolan-3-ols (tetrahydrofuran-3-ols) is dependent upon the oxirane configuration.Cis configuration is more suitable for the formation of the smallest ring.Steric hindrance is not sufficient enough to explain the results.