50638-95-4

Usage

Uses

Used in the Food Industry:
[2-[(3-methyl-2-butenyl)oxy]ethyl]benzene is used as a flavoring agent for its characteristic aniseed-like scent, enhancing the taste and aroma of various food products.
Used in the Fragrance Industry:
In the fragrance industry, [2-[(3-methyl-2-butenyl)oxy]ethyl]benzene is used as a key component to create herbal and sweet scents for perfumes and other scented products.
Used in Natural Medicine:
Methyl chavicol has been studied for its potential antimicrobial and antioxidant properties, making it a subject of interest in the field of natural medicine. It may be used as a natural preservative or for its potential therapeutic benefits.
Used in Food Preservation:
Due to its antimicrobial properties, [2-[(3-methyl-2-butenyl)oxy]ethyl]benzene can be utilized in the food preservation industry to extend the shelf life of perishable items by inhibiting the growth of bacteria and other microorganisms.

InChI:InChI=1/C13H18O/c1-12(2)8-10-14-11-9-13-6-4-3-5-7-13/h3-8H,9-11H2,1-2H3

Upstream product

• 22096-25-9 sodium phenethylate 
• 870-63-3 prenyl bromide 
• 115-18-4 2-methyl-3-buten-2-ol 
• 60-12-8 2-phenylethanol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 598-25-4 Dimethylallene 

Downstream Products

• 42078-65-9 2-phenylethyl 3-methyl-2-butenoate 

Relevant academic research and scientific papers

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.

Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex

(Chemical Equation Presented) Reaction of 2,3-pentadienyl benzoate with benzyl carbamate catalyzed by a 1:1 mixture of (NHC)AuCl and AgOTf in dioxane at 23°C for 5 h led to isolation of (E)-4-(benzyloxycarbonylamino)-2-pentenyl benzoate in 84% yield as a single regio- and diastereomer. Gold(I)-catalyzed hydroamination was effective for a number of N-unsubstituted carbamates and a range of substituted allenes.

Hypervalent (tert-butylperoxy)iodanes generate iodine-centered radicals at room temperature in solution: Oxidation and deprotection of benzyl and allyl ethers, and evidence for generation of α-oxy carbon radicals

1-(tert-Butylperoxy)-1,2-benziodoxol-3(1H)-one (1a) oxidizes benzyl and allyl ethers to the esters at room temperature in benzene or cyclohexane in the presence of alkali metal carbonates. Since this reaction is compatible with other protecting groups such as MOM, THP, and TBDMS ethers, and acetoxy groups, and because esters are readily hydrolyzed under basic conditions, this new method provides a convenient and effective alternative to the usual reductive deprotection. Oxidation with 1a occurs readily with C-H bonds activated by both enthalpic effects (benzylic, allylic, and propargylic C-H bonds) and/or polar effects (α-oxy C-H bonds), generating α-oxy carbon-centered radicals, which can be detected by nitroxyl radical trapping. Measurement of the relative rates of oxidation for a series of ring-substituted benzyl n-butyl ethers 2d and 2p-s indicated that electron-releasing groups such as p-MeO and p-Me groups increase the rate of oxidation, and Hammett correlation of the relative rate factors with the σ+ constants of substituents afforded the reaction constant ρ+ = -0.30. The large value of the isotope effect obtained for the oxidation of benzyl n-butyl ether 2d (k(H)/k(D) = 12-14) indicates that the rate-determining step of the reactions probably involves a high degree of benzylic C-H bond breaking. The effects of molecular dioxygen were examined, and the mechanism involving the intermediacy of the tert-butylperoxy acetal 5 and/or the hydroperoxy acetal 32 is proposed. Particularly noteworthy is the finding that (tert-butylperoxy)iodane 1a can generate the tert-butylperoxy radical and the iodine-centered radical 33a, even at room temperature in solution, via homolytic bond cleavage of the hypervalent iodine(III)-peroxy bond.