97416-85-8

Basic information

• Product Name: ()-tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid
• Synonyms: (1)-Tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid
• CAS NO: 97416-85-8
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 156.1362
• EINECS: 306-833-9
• Mol File: 97416-85-8.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: ()-tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: ()-tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid(97416-85-8)
• EPA Substance Registry System: ()-tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid(97416-85-8)

Safety Data

• Hazardous Substances Data: 97416-85-8(Hazardous Substances Data)

Upstream product

• 27373-86-0 (R)-5,5-dimethyl-4-(3-methyl-but-1-en-c-yl)-dihydro-furan-2-one 
• 80408-87-3 (+)-5,5-dimethyl-4-(3-oxobutyl)tetrahydrofuran-2-one 
• 79-91-4 terebic acid 
• 100052-76-4 (S)-6,6-dimethyl-5-(2-methyl-propenyl)-tetrahydro-pyran-2-one 
• 64-18-6 formic acid 
• 124744-28-1 ((R)-3,3-Dimethyl-oxiranyl)-acetic acid methyl ester 
• 67-66-3 chloroform 
• 10028-15-6 ozone 
• 498-15-7 (+)-Δ³-carene 
• 7664-93-9 sulfuric acid 
• 1187-70-8 (S)-2-isopropylsuccinic acid 
• 6934-77-6 β-carbomethoxy-γ,γ-dimethyl-γ-butyrolactone 
• 34566-25-1 ethyl 2,2-dimethyl-5-oxotetrahydro-3-furancarboxylate 
• 156905-61-2 (S)-4-[1,3]Dioxolan-2-yl-5,5-dimethyl-dihydro-furan-2-one 

Downstream Products

• 93188-02-4 2,2-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid anilide 
• 98546-95-3 Terebinsaeurechlorid 
• 500160-32-7 2,2-dimethyl-5-oxo-tetrahydro-furan-3-carboxylic acid p-toluidide 
• 157007-74-4 (-)-(S)-2,2-dimethyl-5-oxotetrahydro-3-furancarboxylic acid 
• 114475-19-3 4-methyl-3-pentenoic acid phenylamide 

Relevant articles and documents

Sunlight-induced C–C bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins

A sunlight-induced C–C bond formation reactions upon the addition of alcohols/ethers/acetals to olefins proceeded efficiently using di-tert-butyl peroxide (DTBP). The reactions proceeded faster than many of the previously reported sunlight and many conventional lamp photolyses, typically in 3–4 h under irradiation with sunlight, in excellent yield using olefins bearing two electron withdrawing groups (EWGs) (product yield > 95 %) and in good to fair yield with olefins bearing one EWG. The yields observed for some products were ～20 % higher than those obtained using a conventional Xe lamp as the light source, which was confirmed to be due to a light intensity effect. Gram-scale experiments showed similar yields to those observed in their corresponding small-scale experiments.

Continuous-Flow Preparation of γ-Butyrolactone Scaffolds from Renewable Fumaric and Itaconic Acids under Photosensitized Conditions

The method and results described herein concern the photosensitized addition of various alcohols to renewable platform fumaric and itaconic acids under scalable continuous-flow conditions in glass micro- and mesofluidic reactors. Alcohols were used both as reagents and as solvents, thus contributing to a reduced environmental footprint. Process parameters such as the temperature, light intensity, and the nature as well as amount of the photosensitizer were assessed under microfluidic conditions and, next, transposed to a lab-scale mesofluidic reactor connected with an in-line NMR spectrometer for real-time reaction monitoring. Substituted γ-butyrolactones, including spiro derivatives with unique structural features, were obtained with quantitative conversion of the starting materials and in 47-76% isolated yields. The model photoaddition of isopropanol to fumaric acid was next successfully transposed in a pilot-scale continuous-flow photoreactor to further demonstrate scalability.

Microflow photochemistry - A reactor comparison study using the photochemical synthesis of terebic acid as a model reaction

The continuous-microflow photochemical synthesis of terebic acid from maleic acid was investigated in two different microreactor set-ups. The results were subsequently compared to analogue experiments in a conventional chamber reactor. Based on conversion rates, reactor design and energy efficiency calculations, the simple microcapillary reactor showed the best overall performance.