13330-65-9Relevant articles and documents
A Facile Method for Regiospecific Hydroxylation of Resorcinol Diethers
Srebnik, M.,Mechoulam, R.
, p. 1046 - 1048 (1983)
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Kovacic,Kurz
, p. 2011 (1966)
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Anodic coupling of guaiacol derivatives on boron-doped diamond electrodes
Kirste, Axel,Schnakenburg, Gregor,Waldvogel, Siegfried R.
, p. 3126 - 3129 (2011)
The anodic treatment of guaiacol derivatives on boron-doped diamond electrodes (BDD) provides a direct access to nonsymmetrical biphenols, which would require a multistep sequence by conventional methods. Despite the destructive nature of BDD anodes they
Selective monoalkylation of hydroquinone in the presence of SO3H-functionalized ionic liquids as catalysts
Bhongale, Priyanka V.,Joshi, Sunil S.,Mali, Nilesh A.
, p. 4461 - 4471 (2020)
A process aiming at O-alkylation of hydroquinone (HQ), where ionic liquids (ILs) act as catalyst is objectively described. Five SO3H-functionalized ILs having different cations were prepared and characterized by NMR and FTIR techniques. The acidity and thermal stability of ILs were determined by Hammett function and thermogravimetric analysis (TGA), respectively. The catalytic activity of these ILs were tested for O-alkylation of HQ with methanol in 4-methoxyphenol (4MP) in the presence of small amount of benzoquinone (BQ). The effect of reaction parameters such as temperature, time, catalyst loading and substrate concentration on the conversion of HQ and product distribution was examined and optimized to maximize the yield of 4MP using 1,3-disulfonic acid imidazolium hydrogen sulfate (IL2) catalyst. Maximum yield of desired product 4MP 93.79percent was obtained at 338?K temperature, 5.45 × 10–2?mol HQ, 8.33 × 10–3?mol BQ, and 10.37?molpercent catalyst loading in 120?min reaction time. Single-product formation was observed up to 338?K temperature but higher temperature (above 338?K) and longer reaction time resulted in the formation of 2,4-dimethoxyphenol (24DMP) as a by-product. Catalyst recyclability was also established up to the fifth run which showed no declination in its activity.
Reusable and Efficient Polystyrene Immobilized Ionic Liquid Catalyst for Batch and Flow Methylation of Hydroquinone
Bhongale, Priyanka V.,Joshi, Sunil S.,Mali, Nilesh A.
, (2022/01/31)
An environmentally benign process for synthesizing 4-methoxyphenol through methylation of hydroquinone using polystyrene immobilized Bronsted acidic ionic liquid is presented. The catalyst has been characterized by several techniques, such as solid-state NMR, FTIR, and XRD. The morphological properties were analyzed through SEM and TEM analysis. The elemental analysis was performed using EDS and XPS techniques. The catalyst was thermally stable up to 603?K, which was confirmed by TGA. The chemical interaction between ionic liquid and polystyrene was confirmed by measuring the glass transition temperature of pure polystyrene and catalyst. The BET analysis was performed to estimate the catalyst’s surface area, pore size, and pore volume. The recyclability of the proposed new catalyst was established up to five recycle runs in the batch mode. In addition, continuous flow experiments were conducted to test the catalytic activity in terms of catalyst life span and showed excellent stability up to 20?h. The rapid separation, long-term stability, and efficient recycling of synthesized polymeric catalysts make an excellent alternative to the commonly used homogeneous catalysts for selective O-methylation of hydroquinone reaction. The newly developed continuous process for synthesizing 4-methoxyphenol with 100% selectivity suggests good opportunities to reduce energy consumption, which designates a cost-effective process. Graphical Abstract: [Figure not available: see fulltext.]
Synthetic method 4 - alkoxyphenol compounds
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Paragraph 0082-0084, (2021/09/29)
The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.
Oxidation of Electron-Rich Arenes Using HFIP-UHP System
Llopis, Natalia,Baeza, Alejandro
, p. 6159 - 6164 (2020/05/20)
The straightforward oxidation of electron-rich arenes, namely, phenols, naphthols, and anisole derivatives, under mild reaction conditions, is described by means of the use of an environmentally benign HFIP-UHP system. The corresponding quinones or hydroxylated arenes were obtained in moderate to good yields.
