26717-54-4

Basic information

• Product Name: 4-(p-chlorophenyl)dihydrofuran-2(3H)-one
• Synonyms: 4-(p-chlorophenyl)dihydrofuran-2(3H)-one;4-(4-Chlorophenyl)-4,5-dihydrofuran-2(3H)-one;4-(4-Chlorophenyl)dihydro-2(3H)-furanone;4-(4-Chlorophenyl)tetrahydrofuran-2-one
• CAS NO: 26717-54-4
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.63026
• EINECS: 247-913-2
• Mol File: 26717-54-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 357.2°Cat760mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 2.77E-05mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 4-(p-chlorophenyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(p-chlorophenyl)dihydrofuran-2(3H)-one(26717-54-4)
• EPA Substance Registry System: 4-(p-chlorophenyl)dihydrofuran-2(3H)-one(26717-54-4)

Safety Data

• Hazardous Substances Data: 26717-54-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H9ClO2/c11-9-3-1-7(2-4-9)8-5-10(12)13-6-8/h1-4,8H,5-6H2

Upstream product

• 201230-82-2 carbon monoxide 
• 902154-51-2 γ-acetoxycrotonic acid tert-butyl ester 
• 1679-18-1 4-Chlorophenylboronic acid 
• 191019-76-8 2,2-dichloro-3-(4'-chlorophenyl)cyclobutanone 
• 1073-67-2 4-vinylbenzyl chloride 
• 45941-96-6 2-(4-chlorophenyl)-3-hydroxypropene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 152714-07-3 3-(4-chlorophenyl)cyclobutanone 
• 476471-06-4 4-(4-chlorophenyl)-2-methoxytetrahydrofuran 
• 91154-08-4 2-(4-Chloro-phenyl)-butane-1,4-diol 
• 26717-53-3 4-(4-chlorophenyl)furan-2(5H)-one 

Downstream Products

• 89359-16-0 (S)-β-(4-chlorophenyl)-γ-butyrolactone 
• 147224-51-9 β-(R)-(p-chlorophenyl)-γ-butyrolactone 
• 185342-39-6 5-Bromo-4-(4-chloro-phenyl)-5H-furan-2-one 
• 147224-53-1 (R)-ethyl 4-azido-3-(4-chlorophenyl)-1-butanoate 
• 188635-62-3 (R)-4-Azido-3-(4-chloro-phenyl)-butyric acid 
• 63701-55-3 (R)-(-)-baclofen hydrochloride 
• 188635-61-2 (R)-3-(4-Chloro-phenyl)-4-iodo-butyric acid ethyl ester 
• 26717-53-3 4-(4-chlorophenyl)furan-2(5H)-one 

Relevant articles and documents

Efficient Synthesis of γ-Lactones by Cobalt-Catalyzed Carbonylative Ring Expansion of Oxetanes under Syngas Atmosphere

A practical route from oxetane or thietane to γ-(thio)butyrolactone via solvated-proton-assisted cobalt-catalyzed carbonylative ring expansion under syngas atmosphere has been established. A wide variety of γ-(thio)butyrolactones can be afforded in good to excellent yields. The versatility of this method has been well demonstrated in the synthesis of intermediates towards the natural product Arctigenin as well as the pharmaceuticals Baclofen and Montelukast. The observed promoting effect of glycol ether solvent has been rationally interpreted.

Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents

A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids,-butyrolactones, and complex aryl alkyl ethers.

Baeyer–Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones

A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds.