23438-17-7

Upstream product

• 67-56-1 methanol 
• 2101-86-2 p-methylazidobenzene 
• 106-44-5 p-cresol 
• 110391-89-4 8-Methoxy-8-methyl-1,4-dioxa-spiro[4.5]deca-6,9-diene 
• 89345-80-2 4-O-Methyl-4-methyl-p-benzoquinol N-acetylimine 
• 23438-13-3 8-methoxy-3,3,8-trimethyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-2-one 
• 104-93-8 p-methylanizole 
• 89345-78-8 C₁₀H₁₃NO₄S 
• 27451-21-4 N-hydroxy-N-(p-tolyl)acetamide 

Downstream Products

• 29418-58-4 (p-nitrophenylazo)toluene 
• 86255-22-3 (1-Hydroxy-4-methoxy-4-methyl-cyclohexa-2,5-dienyl)-acetic acid methyl ester 
• 74894-53-4 anti-4-methoxy-1,4-dimethyl-2,5-cyclohexadienol 
• 74894-52-3 (Z)-4-methoxy-1,4-dimethylcyclohexa-2,5-dienol 
• 6562-26-1 4'-methyl-2,4-dinitroazobenzene 
• 14786-82-4 4-hydroxy-2-methylanisole 
• 106-44-5 p-cresol 

Relevant academic research and scientific papers

Site-selective 1,3-double functionalization of arenes using: Para -quinol, C-N, and C-C/C-P three-component coupling

A catalytic and site-selective approach has been demonstrated for dual functionalization of arenes via cross-coupling reactions of p-quinols with amines and isocyanides/phosphites. The strategy enables the production of a series of 3-amino-benzamides and

Zinc-catalyzed regioselective C-P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

The zinc triflate-catalyzed highly regioselective C-P cross coupling reaction of p-quinol ethers with secondary phosphine oxides is reported. The reaction provides a facile alternative method for the synthesis of 2-phosphinylphenols in good to high yields. Mechanistically, zinc triflate may serve as an oxophilic σ-Lewis acid to activate the C-O bond in p-quinol ether first. Then the regioselective attack of the phosphorus nucleophile at the α-carbon position takes place to form the C-P bond and give the product. In addition, α-alkynyl substituted p-quinol ethers also react with secondary phosphine oxides in the same reaction mode to give 6-alkynyl 2-phosphinylphenols in the presence of the zinc catalyst.

Site-Selective Iron(III) Chloride-Catalyzed Arylation of 4-Aryl-4-methoxy-2,5-cyclohexadienones for the Synthesis of Polyarylated Phenols

The iron(III) chloride-catalyzed Friedel–Crafts arylation of 4-aryl-4-methoxy-2,5-cyclohexadienones, which were easily prepared by the phenyliodine(III) diacetate (PIDA)-mediated oxidation of 4-arylphenols in methanol, proceeded site-selectively to form meta-terphenyl (2,4-diarylphenol) derivatives in good yields. The subsequent PIDA-mediated oxidation and iron(III) chloride-catalyzed Friedel–Crafts arylation of the resulting products gave the corresponding 2,4,6-triarylphenol derivatives. The present method provides useful highly substituted polyarylated compounds. (Figure presented.).

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

A detour route for meta functionalization of phenols

Cyclohexadienones participate in a two-step procedure, a Michael addition followed by aromatization, providing hitherto difficult-to-synthesize meta-functionalized phenol derivatives in good yield. Application of the developed approach is exemplified by synthesizing C-aryl acetophenones, C-aryl glycines, and elemicin - an allylphenol natural product. Georg Thieme Verlag Stuttgart · New York.

Meta-selective substitution of phenols with indoles via one-pot oxidative dearomatization-Michael addition-aromatization

An oxidative coupling strategy involving hypervalent organoiodine-induced oxidative dearomatization of 4-substituted phenols, Br?nsted acid catalyzed Michael addition with indoles, and aromatization has been developed. The one-pot reaction provides an eff

Stereoselectivity control by oxaspiro rings during Diels-Alder cycloadditions to cross-conjugated cyclohexadienones: The syn oxygen phenomenon

The diastereofacial selectivity operating in Diels-Alder additions involving spirocyclic cross-conjugated cyclohexadienones with dienes of varying reactivity has been investigated. The study has included the ether series 1a-c as well as the lactone/ketone pair 2a/2b. In all cases, the preferred [4+2] cycloaddition pathway consisted of bonding from that π-surface syn to the oxygen atom. 4-Substituted-4-methyl-2,5-cyclohexadienones (monocyclic systems) were also examined and found to undergo bond formation preferentially from the face bearing the more electron-withdrawing of the two groups at the 4 position. Kinetic parameters were determined for the cycloaddition of 1a and 2a to cyclopentadiene. The rate acceleration profile of solvents was in the order CF3CH2OH ? CH3CN～CH2Cl 2 for the production of 9a from 1a and CF3CH2OH ? CH2Cl2 > CH3CN for the production of 21a from 2a, respectively. This spread in polarity had no major impact on product distribution, a phenomenon also reflected in the behavior of 4-substituted-4-methyl-2,5-cyclohexadienones under comparable conditions. Theoretical assessment of these experimental facts was undertaken at the HF/6-31G* level. The facial selectivity is understandable in terms of the secondary interaction between the HOMO of the diene and LUMO of the dienophile as well as the effective hyperconjugation between the newly forming bond and the 4-anti-C-C σ-orbital due to the more electron-donating bond, as defined by the Cieplak model.

Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases

Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)2N- M+, generated in situ from N(TMS)3 and M+ F- or RO- Na+. When F- is used in a catalytic amount, silylated α-(trifluoromethyl)carbinols are obtained: In this case, the four-component system HCF3/N(TMS)3/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)3/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of awl disulfides whereas N(SiMe3)3/F- is Well suited to that of aliphatic disulfides.

Synthesis of polysubstituted bicyclo[3.3.1]nonane-3,7-diones from cyclohexa-2,5-dienones and dimethyl 1,3-acetonedicarboxylate

Oxidation of polysubstituted phenols with phenyliodonium diacetate gives cyclohexa-2,5-dienones, which on reaction with dimethyl 1,3-acetonedicarboxylate afford double-Michael-addition derivatives, whose hydrolysis and decarboxylation provides polysubstituted bicyclo[3.3.1]nonane-3,7-diones. For steric and/or electronic reasons, the Michael reaction only works with 3,5-unsubstituted or 3-substituted cyclohexa-2,5-dienones, if the substituent is not an electron-releasing or a good electron-withdrawing group. Hydrolysis and decarboxylation of the double-Michael adducts from 2,4,4- or 2,4,4,6-substituted cyclohexa-2,5-dienones gives only products of partial hydrolysis and decarboxylation, which exist exclusively in the enol form. (C) 2000 Elsevier Science Ltd.

Oxidation with hypervalent iodine reagents. Part II: Novel cyclohexadienones as precursors for the synthesis of anthraquinones

The oxidation of substituted phenols with phenyliodonium diacetate in methanol was found to afford 2,4-cyclohexadienones, 2,5-cyclohexadienones or mixtures of isomers, depending on the substrate being oxidized. Annulation of these cyclohexadienones with the anion of 3-cyanophthalide afforded anthraquinones in high yields.