37055-79-1

Usage

InChI:InChI=1/C13H12O2/c1-15-13-9-11(7-8-12(13)14)10-5-3-2-4-6-10/h2-9,14H,1H3

Upstream product

• 7368-78-7 4-bromoguaiacol 
• 591-51-5 phenyllithium 
• 63057-72-7 2-benzyloxy-5-bromoanisole 
• 125101-79-3 2-benzyloxy-5-phenylphenol 
• 110391-82-7 4-Hydroxy-2-methoxy-4-phenyl-cyclohexa-2,5-dienone 
• 125101-83-9 4-benzyloxy-3-methoxybiphenyl 
• 17423-55-1 3,4-dimethoxy-1,1'-biphenyl 
• 71-43-2 benzene 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1404575-82-1 C₁₄H₁₄O₃ 

Relevant academic research and scientific papers

An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols

The development of a novel Suzuki-Miyaura method has been achieved to allow the efficient arylation of bromophenols. A range of functionality is tolerated with regard to the boronic acid coupling partner and the reaction exhibits complete chemoselectivity for the Caryl-Br bond versus the Caryl-Cl bond in the aryl halide input. The experimental protocol features a short reaction time of 15 min, utilizes inexpensive Pd/C as a catalyst, and is conducted with water as the solvent.

Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations

This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-en-capsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused microwave heating whilst applying an external cooling source. This enables a lower than normal bulk temperature to be maintained throughout the reaction period leading to significant improvements in the overall yield and purity of the reaction products. Additional aspects of this novel heating protocol are discussed in relation to the prolonged lifetime and enhanced reactivity of the immobilised catalyst system.

WB4101-related compounds: New, subtype-selective α1- adrenoreceptor antagonists (or inverse agonists?)

Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues (compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-be

A new entry to the synthesis of 1,2-benzenediol congeners

1,2-Benzenediols were synthesized via 1,1-bis(ethylthio)-3-cyclohexen-2-one derivatives, which were prepared by condensation of 1,1-bis(ethylthio)-2-propanone with Mannich bases. Regioselective preparation of their monoethers was also achieved.

A NEW ENTRY TO 1,2-BENZENEDIOL CONGENERS

1,2-Benzenediols and their monoethers were efficiently prepared from α,α-bis(ethylthio)cyclohexenones which were constructed by the C3+C3 annulation of 1,1-bis(ethylthio)propan-2-one and the Mannich bases. KEYWORDS 1,2-benzenediol; aromatic synthesis; annulation; aromatic compound; acetal

REGIOSELECTIVITY OF NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION IN THE BIPHENYL SERIES. PHOTOHYDROLYSIS OF SOME DIMETHOXYNITROBIPHENYLS

Anaerobic photolysis of dimethoxynitrobiphenyls IIIa-VIa in aqueous alkaline tert-butanol gave products of nucleophilic photodubstitution of methoxyl by hydroxide anion, while the dimethoxybiphenyls Ia and IIa were found unreactive.Regioselectivity of the reaction was examined in view of a possible "extended meta activation" by the nitro group.The most reactive substrate IIIa gives both C-3 and C-4 substitution products with an unsubstantial preference for the latter, which opposes the "extended meta selectivity" rule.All of the other compounds obey the rule, and 3,4-dimethoxy-3'-nitrobiphenyl (IVa) even displayed absolute selectivity by yielding C-3 substituted compound as the only product. 2,5-Dimethoxy substituted compounds underwent photosubstitution with much lower quantum yields than their 3,4-substituted counterparts, most probably due to some steric hindrance of conjugation.Similarly, 3-nitro-substituted biphenyls exhibited much lower overall reactivity than 4-nitro derivatives.

Structural and Solvent/Electrolyte Effects on the Selectivity and Efficiency of the Anodic Oxidation of Para-Substituted Aromatic Ethers. An Efficient Route to Quinol Ether Ketals and Quinol Ethers

The anodic oxidations of the methyl ethers of p-arylphenols C6H4, o-C6H4, o-HO2CC6H4>, the 2-hydroxyethyl ethers of p-arylphenols , and the 2-hydroxyethyl ethers of p-alkylphenols and 4-methyl-1-naphthol were studied.The p-aryl aromatic ethers underwent anodic oxidation in good yield to give the corresponding p-quinol ether ketals.The ratio of nuclear to side-chain products from anodic oxidation of p-alkylanisole derivatives is dependent upon the electrolysis conditions.The 2-hydroxyethyl ether derivatives of p-alkylphenols markedly favor the formation of nuclear oxidation products - providing a useful route to the corresponding p-quinol ether ketals.In addition, methanolic potassium fluoride improves the efficiency of these anodic oxidation processes by about 400percent relative to methanolic potassium hydroxide.These reactions were performed at a constant current (1.0-2.0 A) in a single cell and serve as preparative routes to p-quinol ether ketals and quinol ethers via acid hydrolysis.