22530-98-9

Basic information

• Product Name: 4-BENZYLOXOLAN-2-ONE
• Synonyms: 4-BENZYLOXOLAN-2-ONE;4-Benzyldihydrofuran-2(3H)-one;2(3H)-Furanone, dihydro-4-(phenylmethyl)-
• CAS NO: 22530-98-9
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21178
• EINECS: -0
• Mol File: 22530-98-9.mol

Chemical Properties

• Melting Point: 45-46 °C(Solv: ethanol (64-17-5))
• Boiling Point: 155-160 °C(Press: 1 Torr)
• Appearance: /
• Density: 1.122 g/cm3
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BENZYLOXOLAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXOLAN-2-ONE(22530-98-9)
• EPA Substance Registry System: 4-BENZYLOXOLAN-2-ONE(22530-98-9)

Safety Data

• Hazardous Substances Data: 22530-98-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
4-BENZYLOXOLAN-2-ONE is used as a fragrance ingredient for its pleasant floral scent, adding value to personal care products and perfumes by enhancing their olfactory appeal.
Used in Organic Synthesis:
4-BENZYLOXOLAN-2-ONE is utilized as a chemical intermediate in the preparation of pharmaceuticals and agrochemicals, playing a crucial role in the synthesis of various organic compounds.
Used in Industrial Processes:
4-BENZYLOXOLAN-2-ONE is used as a chelating agent for its ability to bind and remove metal ions from solutions, which is beneficial in various industrial applications to improve process efficiency and product quality.

Upstream product

• 87439-00-7 3-(ethoxycarbonyl)-2-benzylidenepropanoic acid 
• 16720-76-6 4-(phenylmethyl)-2(5H)-furanone 
• 112654-60-1 (E)-cinnamyl bromoacetate 
• 78939-70-5 4-Benzyl-5-ethoxy-dihydro-furan-2-one 
• 67-56-1 methanol 
• 67-64-1 acetone 
• 497-23-4 2-buten-4-olide 
• 100-44-7 benzyl chloride 
• 55262-02-7 3-benzyl-cyclobutanone 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 7287-39-0 4-(2-vinyloxy-ethoxy)-butan-1-ol 
• 96181-46-3 3-(ethoxycarbonyl)-4-phenylbut-3-enoic acid 
• 112895-74-6 5-hydroxy-4-benzylbutenolide 
• 118527-76-7 trans-3-benzyl-5-(trimethylsilyl)-cyclohexanone 

Downstream Products

• 96540-46-4 4-benzyl-3-phenylthio-4,5-dihydrofuran-2(3H)-one 
• 133496-51-2 β-(bromomethyl)-γ-phenylbutyric acid 
• 112895-79-1 Sodium; 3-hydroxymethyl-4-phenyl-butyrate 
• 374717-36-9 propyl 3-benzyl-4-hydroxybutanoate 
• 126434-65-9 (S)-(-)-β-benzyl-γ-butyrolactone 
• 126434-64-8 (R)-dihydro-4-(phenylmethyl)furan-2(3H)-one 
• 16720-76-6 4-(phenylmethyl)-2(5H)-furanone 
• 96540-49-7 4-benzyl-3-phenylsulfinyl-4,5-dihydrofuran-2(3H)-one 
• 1381783-43-2 4-benzyl-3-diazo-dihydrofuran-2-one 
• 1443013-38-4 4-benzyl-2-(trimethylsiloxy)-4,5-dihydrofuran 
• 1443013-62-4 (α S,βR)-β-benzyl-α-(1-naphthyl)-γ-butyrolactone 

Relevant articles and documents

Synthesis method of butyrolactone compound

The invention relates to a synthesis method of a butyrolactone compound. The synthesis method comprises the following step: in the presence of a solvent and a cobalt catalyst, converting an oxetane compound shown as general formula I into a butyrolactone compound shown as general formula II through carbonyl insertion ring expansion reaction in an atmosphere of CO and H2. Compared with an existingmethod for synthesizing butyrolactone through oxetane carbonylation ring expansion reaction in a carbon monoxide atmosphere, the synthesis method of a butyrolactone compound provided by the inventionhas the advantages of excellent catalytic activity, excellent chemical selection, wide substrate applicability, mild reaction conditions and the like; compared with other methods for synthesizing butyrolactone compounds, the method provided by the invention has the advantages of wide substrate range, high atom economy, no need of noble metal catalysis and the like, therefore the method has a wideapplication prospect.

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.

Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst

Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.

Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration

Intermolecular Rh-catalyzed reactions of cyclic α-diazocarbonyl compounds with chemoselectivity over β-hydride elimination are described. These methods represent the first general intermolecular reactions of Rh-carbenoids that are selective over tertiary

Regioselective lactonization of unsymmetrical 1,4-diols: An efficient access to lactone lignans

A Cp*Ru-based bifunctional catalyst system (Cp* = η5-C5(CH3)5) with a suitably-designed PN ligand (PN = chelating tertiary phosphine-protic amine ligand) has been developed for a regioselective lactonization of

Tin-free generation of alkyl radicals from alkyl 4-pentynyl sulfides via homolytic substitution at the sulfur atom

Homolytic substitution at the sulfur atom of β-(phenylsulfanyl)vinyl radicals, obtained by radical reaction of benzenethiol with easily accessible alkyl 4-pentynyl sulfides, is a mild, effective, tin-free route for the generation of all types of alkyl radicals. This protocol can be employed in reductive defunctionalizations as well as cyclizations onto both electron-rich and electron-poor C-C double bonds.

Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases

Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.

Baeyer-Villiger oxidation in compressed CO2

The aerobic Baeyer-Villiger oxidation of a wide range of ketones, both cyclic and acyclic to the corresponding esters or lactones can be efficiently carried out in compressed carbon dioxide in the presence of an aldehyde as co-reductant.

A short synthesis of biologically active lignan analogues

β-Benzyl-γ-butyrolactones were synthesized in four transition metal catalysed reactions from butynediol, and alkylated to afford new, biologically active lignan analogues.

Radical cyclization on solid support: Synthesis of γ-butyrolactones

Synthesis of γ-butyrolactones using radical cyclization on solid-phase has been achieved. Polymer-supported β-bromoethylacetals were treated with tributyltin hydride in the presence of a catalytic amount of α,α'- azobisisobutyronitrile to generate intermediate carbon radicals which cyclize onto the intramolecular carbon-carbon double bond. The cyclization products were released by Jones oxidation from resin to give γ-butyrolactones in good yields.