95122-53-5

Upstream product

• 142-30-3 2,5-dihydroxy-2,5-dimethyl-3-hexyne 
• 111258-54-9 tetrahydro-2,3,5,5-tetramethyl-2,3-furandiol 
• 5455-94-7 2,2,5,5-tetramethyltetrahydro-3-oxofuran 
• 17918-67-1 2-methyl-2-hydroxy-4-pentanone oxime 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 

Downstream Products

• 964-83-0 4-methyl-3-penten-2-one (2,4-dinitrophenyl)hydrazone 

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.