1515-81-7

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 44, p. 2337, 1966 DOI: 10.1139/v66-350

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

Upstream product

• 121-98-2 methyl 4-methoxybenzoate 
• 124-41-4 sodium methylate 
• 824-94-2 p-methoxybenzyl chloride 
• 123-63-7 paracetaldehyde 
• 67-56-1 methanol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 110-82-7 cyclohexane 
• 23304-25-8 p-methoxyphenyldiazomethane 
• 17953-95-6 3-p-Anisyl-1,1,2,2-tetramethylcyclopropane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 27490-32-0 tributyl(methoxymethyl)stannane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 5925-50-8 O-methyl 4-methoxybezenecarbothioate 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 26434-43-5 meso-4,α,4',α'-tetramethoxy-bibenzyl 
• 26434-43-5 C₁₈H₂₂O₄ 
• 114137-90-5 {(1R,2R)-2-[(4R,5S,6R)-6-{(1R,3R)-3-Benzyloxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-dimethyl-silane 
• 114137-90-5 {(1R,2R)-2-[(2R,4R,5S,6R)-6-{(1R,3R)-3-Benzyloxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-dimethyl-silane 
• 123493-54-9 tert-Butyl-((1R,2R)-1-ethyl-2-{(3R,5R,6S,7S,8R)-1-(4-methoxy-phenyl)-3,5,7-trimethyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-2,9,10-trioxa-bicyclo[4.3.1]dec-8-yl}-propoxy)-dimethyl-silane 
• 114137-91-6 (2R,4R)-4-[(2R,4S,5S,6R)-6-[(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-butyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentan-2-ol 
• 111874-57-8 1-methoxy-4-(1-methoxybut-3-en-1-yl)benzene 
• 134744-42-6 Benzoic acid 2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-5-vinyl-[1,3]dioxolan-4-yl]-ethyl ester 
• 88040-12-4 (2S,3R,4R,5R)-2,3-epoxy-1-hydroxy-4,5-(4-methoxybenzylidenedioxy)-2,4-dimethylheptane 
• 88040-08-8 (2S,3R)-1-benzoyloxy-2,3-<(R)-(4-methoxybenzylidene)dioxy>-2-methylpentane 
• 123-11-5 4-methoxy-benzaldehyde 
• 17179-20-3 p-methoxybenzyllithium 
• 105-13-5 4-Methoxybenzyl alcohol 
• 99232-39-0 C₈H₉KO 

Relevant academic research and scientific papers

Physical organic chemistry of transition metal carbene complexes. 24. Thermodynamic and kinetic acidities of phenyl-substituted (benzylmethoxycarbene)pentacarbonylchromium(0) complexes. Is there a transition-state imbalance?

A kinetic study of the reversible deprotonation of phenyl-substituted (benzylmethoxycarbene)pentacarbonylchromium(0) complexes by OH- and by a series of primary aliphatic and a series of secondary alicyclic amines in 50% MeCN-50% water (v/v) at 25°C is reported. Bronsted αCH values (dependence on carbene complex acidity) and βB values (dependence on amine basicity) were determined. According to current notions about proton transfers involving carbon acids activated by φ-acceptors, αCH was expected to substantially exceed βB, the result of transition-state imbalances that are characteristic of such reactions. However we find that αCH and βB have essentially the same values, which are close to0.5. It is shown that these findings do not indicate the absence of an imbalance but rather suggest that the manifestation of the imbalance is masked by the φ-donor effect (3H-Z ? 3H-Z±) of the methoxy group.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Site-Selective Alkoxylation of Benzylic C?H Bonds by Photoredox Catalysis

Methods that enable the direct C?H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C?N and C?C bond formation. In particular, almost all methods for the incorporation of alcohols by C?H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C?H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C?O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.

Nickel-catalyzed intelligent reductive transformation of the aldehyde group using hydrogen

The selective transformation of the aldehyde group (-CHO) in multifunctional oxygenates is a key challenge in the development of sustainable biomass feedstock. Herein, a smart Ni-MFC catalyst was developed from a 2D Ni-based metal-organic framework (MOF), which efficiently promoted the transformation of -CHO in the presence of H2 to a methyl group (-CH3) via the reductive etherification and hydrogenolysis of the C-O ether bond in methanol. Moreover, the catalytic process could be controlled to directionally produce methyl ether (-CH2OR) using the reductive etherification protocol. For the catalytic reduction of vanillin, the Ni-MFC-700 catalyst guaranteed the full conversion of vanillin and 96.5% yield of the desired 2-methoxy-4-methylphenol (MMP), while the Ni-MFC-500 catalyst afforded about 82.7% yield of 4-(methoxymethyl)-2-methoxyphenol in methanol solvent. This is a novel and promising approach for the valorization of multifunctional oxygenates and biomass-derived platform compounds.

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.

Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones

Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H2, R-OH or H2O generates the required Br?nsted acid in a reversible, “turn on” manner. The method is not only a complementary metal-free reductive etherification, but also a niche procedure for ethers that would be either synthetically inconvenient or even intractable to access by alternative synthetic protocols.

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.

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%.

Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols

Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions.

Direct synthesis of ethers from aldehydes and ketones. One-pot reductive etherification of benzaldehydes, alkyl aryl ketones, and benzophenones

Benzyl alcohols formed by the reduction of benzaldehydes, alkyl aryl ketones, and benzophenones with sodium tetrahydridoborate in alcohols undergo in situ etherification with the solvent in the presence of a catalytic amount of HCl. Thus the process may be regarded as one-pot transformation of carbonyl compounds into the corresponding benzyl ethers. The yields of ethers depend on the substituent nature in the aromatic fragment of the initial carbonyl compound and on the alcohol used as reduction medium.