13395-86-3Relevant academic research and scientific papers
Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp 2)-H Alkylation with Nitroalkanes
Dinh, Andrew N.,Noorbehesht, Ryan R.,Toenjes, Sean T.,Jackson, Amy C.,Saputra, Mirza A.,Maddox, Sean M.,Gustafson, Jeffrey L.
supporting information, p. 2155 - 2160 (2018/09/29)
We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp 2)-H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing
Selective water-based oxychlorination of phenol with hydrogen peroxide catalyzed by manganous sulfate
Xin, Hongchuan,Yang, Shilei,An, Baigang,An, Zengjian
, p. 13467 - 13472 (2017/03/11)
An efficient method for the selective oxychlorination of phenol to 2,4-dichlorophenol catalyzed by manganous(ii) sulfate is developed using hydrogen chloride as a chlorinating source, hydrogen peroxide as an oxidant and water as a solvent. The catalyst has high activity and selectivity under mild conditions. The products are automatically isolated from aqueous solution, which also contains the catalyst at the end of the reaction, and hence product separation and catalyst recycling are both simple in this system. The performance of manganous(ii) sulfate with the oxidative chlorinating system HCl/H2O2 indicates that this is a promising synthetic method for the manufacture of various 2,4-dichlorophenol derivatives.
2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride
Saper, Noam I.,Snider, Barry B.
, p. 809 - 813 (2014/04/03)
2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.
Cyclodienones. X. Reaction of Halo-cyclohexadien-1-ones with Phenols in the Presence of α-Picoline and Preparation of 4-Hydroxy- and 2-Hydroxyphenyl Aryl Ethers
Tashiro, Masashi,Itoh, Takashi,Fukata, Gouki
, p. 416 - 420 (2007/10/02)
Reaction of 4-halocyclohexadienones such as 4-bromo-(1a), 4-chloro-2,4,6-tri-t-butyl-(1b), 2,4-dichloro-4,6-di-t-butyl-2,5-cyclohexadien-1-one, and 2,4-dichloro-2,6-di-t-butyl-3,5-cyclohexadien-1-one with phenols in the presence of α-picoline was carried out under various conditions.The reaction of 1a and 1b with phenols afforded the corresponding 2-aryloxy-4,6-di-t-butyl phenols together with various by-products.The AlCl3 catalyzed trans-t-butylation of 2-aroxy-4,6-di-t-butyl-phenols, which were obtained by the above reaction, afforded the corresponding 2-hydroxyphenyl aryl ethers.The similar reaction of 4-aroxy-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-ones also afforded the corresponding 4-hydroxyphenyl aryl ethers.
Phenol transalkylation process
-
, (2008/06/13)
Phenols having an unsubstituted ortho position are transalkylated in the ortho position by mixing them with an ortho-alpha-branched alkylphenol (e.g., 2,6-di-sec-butylphenol) and an aluminum phenoxide catalyst and heating the mixture to 100°-350°C., preferably in a closed system and in the presence of olefin corresponding in structure to the ortho-alpha-branched alkyl group.
