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Upstream product

• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 65109-39-9 4-(2-(2,6-dimethoxyphenoxy)-1-hydroxyethyl)-2,6-dimethoxyphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 67-56-1 methanol 
• 6638-05-7 2,6-dimethoxy-4-methylphenol 
• 111-27-3 hexan-1-ol 

Relevant academic research and scientific papers

Facile and Selective Cross-Coupling of Phenols Using Selenium Dioxide

Nonsymmetric biphenols are important structural motifs in organic chemistry. Therefore, an easy and versatile protocol for oxidative cross-coupling is essential to generate these so-called “privileged ligands”. We developed an efficient and selective oxidative pathway to synthesize 2,2′-biphenols as well as 2,4′- and 4,4′-biphenols. The use of selenium dioxide, a stable, powerful, and commercially available oxidizer, in 1,1,1,3,3,3-hexafluoroisopropanol allowed the oxidative coupling of alkyl-, alkoxy-, and halogen-substituted phenols.

Profiling of the formation of lignin-derived monomers and dimers from: Eucalyptus alkali lignin

Lignin is a renewable and the most abundant aromatic source that can be used for extensive chemicals and materials. Although approximately 50 million tons of lignin are produced annually as a by-product of the pulp and paper industry, it is currently underutilized. It is important to know the structural features of technical lignin when considering its application. In this work, we have demonstrated the formation of low-molecular-weight constituents from hardwood (Eucalyptus) lignin, which produces much more low-molecular-weight constituents than softwood (spruce) lignin, after a chemical pulping process, and analyzed the micromolecular compositions in the alkali lignin after fractionation by dichloromethane (DCM) extraction. By applying analytical methods (gel-permeation chromatography, 2D NMR and GC-MS) with the aid of evidence from authenticated compounds, a great treasure trove of lignin-derived phenolic compounds from Eucalyptus alkali lignin were disclosed. Except for some common monomeric products, as many as 15 new lignin-derived monomers and dimers including syringaglycerol, diarylmethane, 1,2-diarylethanes, 1,2-diarylethenes, (arylvinyl ether)-linked arylglycerol dimers and isomeric syringaresinols were identified in the DCM-soluble fraction. Regarding the formation and evolution of the Cα-condensed β-aryl ether structure, a novel route that is potentially responsible for the high content of β-1 diarylethenes and diarylethanes in the lignin low-molecular-weight fraction, in addition to the β-1 (spirodienone) pathway, was proposed. This work not only provides novel insights into the chemical transformation of S-G lignin during the alkali pulping process, but also discovered lignin-derived phenolic monomers and dimers that can potentially be used as raw materials in the chemical or pharmaceutical industries. This journal is

Selective oxidation of phenols to hydroxybenzaldehydes and benzoquinones with dioxygen catalyzed by polymer-supported copper

Oxidation of 2,6-disubstituted 4-methylphenols with dioxygen by using a CuCl2-poly(4-methyl-4′-vinyl-2,2′-bipyridine) catalyst gave the corresponding 4-hydroxybenzaldehydes in high yields. The activity of the catalyst and the selectivity of the products significantly depended on the reaction conditions and the composition of the catalyst. When the molar ratio of the bipyridine unit of the polymer ligand to Cu was unity, i.e., N/Cu = 2, the best results were obtained. Moreover, the reaction is likely to be promoted by coordination of the products to the catalyst. Similarly, 2,3,6-trimethylphenol and related compounds were converted to p-benzoquinones selectively with a CuCl2-poly(4-vinylpyridine) catalyst. These polymer-supported catalysts were readily recovered and are reusable without noticeable decrease of their activity.

Choice of Manganese(III) Complexes for the Synthesis of 4,4'-Biphenyldiols and 4,4'-Diphenoquinones

2,6-Disubstituted phenols are oxidized with tris(2,4-pentanedionato)manganese(III), , in glacial acetic acid to give the corresponding 4,4'-biphenyldiols in high yields, whereas similar reactions using manganase(III) acetate, , instead of quantitatively yield the corresponding 4,4'-diphenoquinones.Cross-coupling reactions of 2,6-di-t-butylphenol and other substituted phenols afford the corresponding cross-coupled 4,4'-biphenyldiols and 4,4'-diphenoquinones together with oxidation products derived from them starting phenols themselves.The advantageous use of and Mn(OAc)3> in the ubiqitous phenol coupling reaction is discussed.