21998-86-7

Usage

Type of compound

Organic compound

Usage

Flavoring agent in the food industry, production of perfumes and fragrances, synthesis of pharmaceuticals and agrochemicals

Aroma

Sweet and creamy

Color

Colorless to pale yellow

Odor

Pleasant

Properties

Insecticidal, antibacterial

InChI:InChI=1/C9H12O2/c1-10-7-8-5-3-4-6-9(8)11-2/h3-6H,7H2,1-2H3

Upstream product

• 90-01-7 salicylic alcohol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 612-16-8 (2-methoxyphenyl)methanol 
• 578-57-4 2-bromoanisole 
• 27490-32-0 tributyl(methoxymethyl)stannane 
• 77-78-1 dimethyl sulfate 
• 135-02-4 ortho-anisaldehyde 
• 914300-09-7 1-(chloromethoxymethyl)-2-methoxybenzene 
• 69-72-7 salicylic acid 
• 1441-87-8 salicyloyl chloride 
• 910251-11-5 potassium trifluoro(methoxymethyl)boranuide 
• 766-51-8 2-Chloroanisole 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 125258-70-0 o-methoxy-N,O-dimethylhalostachine 
• 99232-42-5 o-anisyllithium 
• 99232-41-4 C₈H₉KO 
• 99232-40-3 C₈H₉CsO 
• 22800-73-3 α-methyl-o-methoxybenzyl methyl ether 
• 159754-77-5 1-methoxy-2-(1-methoxypentyl)benzene 
• 13513-82-1 1-(2-methoxyphenyl)ethanol 
• 942-54-1 2-(4-methoxyphenyl)propanoic acid 

Relevant academic research and scientific papers

An Application of nJ(CH2,H) and 5J(OH,H) Long-Range Couplings in the Conformational Analysis of 2-Hydroxybenzyl Methyl Ether in Various Solvents. Computational Strategies for Spectral Analysis and Determination of Association Thermod

1H NMR spectra of 2-hydroxy- and 2-methoxy-benzyl methyl ethers were measured in various solvents and solvent mixtures.Precise nJ(CH2,H), where n = 4, 5 or 6, and 5J(OH,H) long-range couplings were applied to the characterization of

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.

Methoxymethylation and benzyloxymethylation of aryl bromides

The methoxymethylation and benzyloxymethylation of aryl bromides methodology was reported here. The transition metal free, high yielding one pot procedure will be useful for synthetic community.

A synthetic method of the compound animal pen ether class

The invention relates to a synthetic method of a benzyl ether compound. The synthetic method is used for avoiding environmental pollution caused by conventional benzyl ether compound synthetic methods. The synthetic method comprises following steps: step 1, a benzyl silane compound, an oxidizing agent, and a light reaction catalyst are delivered into a reactor, the reactor is vacuumized, and is filled with nitrogen for protection, an alkali compound and an alcohol reagent are delivered into the reactor through syringes, the reactor is exposed to visible light, reaction is carried out at room temperature with magnetic stirring, after reaction, an obtained reaction solution is filtered, and a liquid obtained via filtration is subjected to condensation so as to remove solvents and obtain a concentrated solution; and step 2, the concentrated solution is subjected to silica-gel column chromatography for separation and purification so as to obtain the benzyl ether compound, wherein a mixed solution of petroleum ether and ethyl acetate is taken as an eluent. Reaction conditions are mild; operation is simple and convenient; reaction yield is high; and the maximum reaction yield can be 93%.

Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters

Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity. An assist from Al: A bifunctional catalyst system consisting of a Ru/phosphine complex and aluminum triflate allows selective hydrogenation of esters to ethers. A variety of lactones were reduced to the desired products in good yields. The catalyst further provides a general method for the reduction of linear esters and reductive etherification of carboxylic acids with alcohols.

Methoxy-substituted α, n-didehydrotoluenes. photochemical generation and polar vs diradical reactivity

The photoreactivity of differently substituted (chloromethoxybenzyl)trimethylsilanes in alcohols and alcohol/water mixtures has been investigated by means of a combined computational and experimental approach. Subsequent elimination of the chloride anion and the trimethylsilyl cation gives the corresponding methoxy-substituted α,n-didehydrotoluenes (α,n-MeO-DHTs). The rate of desilylation is evaluated through the competition with arylation via phenyl cation (ca. 108s-1). α,2-MeO- and α,4-MeO-DHTs show a purely radical behavior (H abstraction from the solvent, methanol), while α,3-MeO-DHT shows mainly a ionic chemistry, as when the parent α,3-DHT is thermally generated. This is likely due to triplet-singlet surfaces crossing occurring during desilylation.

TiCl4-activated selective nucleophilic substitutions of tert-butyl alcohol and benzyl alcohols with π-donating substituents

TiCl4-activated selective nucleophilic substitution reactions of tert-butyl alcohol and benzyl alcohols with π-donating substituents in the presence of primary and secondary alcohols can be carried out with various oxygen, nitrogen and carbon nucleophiles in good yields.

HYDROXYMETHYLBORON COMPOUNDS

The present invention provides compounds which are useful as safe substitutes for the organotin reagent used in coupling reaction for the oxymethylation of aromatic rings, such as alkoxymethylation or hydroxymethylation, with a palladium catalyst and which can dispense with chromatographic purification with silica gel in the production and are suitable for mass production; and compounds applicable even to the oxymethylation of aromatic ring substrates which do not permit coupling reaction by conventional technique or have low reactivity.

[1,2]-Wittig rearrangement from chloromethyl ethers

The reaction of different chloromethyl ethers 1 with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (2.5 mol %) in THF at 0 °C leads to the corresponding α-lithiomethyl ether intermediates, through a chlorine-lithium exchange, which spontaneously undergo a clean [1,2]-Wittig rearrangement affording the expected homobenzylic alcohols 2. This is the first version of this rearrangement starting from easily available chloromethyl ethers.

Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation

Mild and efficient S-methylation of thiols and o-methylation of phenols and naphthals occurs with dimethyl sulfate (DMS) supported on basic alumina under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.