1988-89-2

Usage

Purification Methods

Crystallise the phenol from pet ether. S-(+)-enantiomer has []D +10.3o (*C6H6). [Okamoto et al. Bull Chem Soc Jpn 39 303 1966.]

InChI:InChI=1/C14H14O/c1-11(12-5-3-2-4-6-12)13-7-9-14(15)10-8-13/h2-11,15H,1H3/t11-/m1/s1

Upstream product

• 39477-86-6 1-phenyl-1-(2-hydroxyphenyl)ethene 
• 100-42-5 styrene 
• 108-95-2 phenol 
• 4237-44-9 2-(1-phenylethyl)phenol 
• 98-85-1 1-Phenylethanol 
• 60-12-8 2-phenylethanol 
• 672-65-1 (1-chloroethyl)benzene 
• 4333-75-9 1-(4-methoxyphenyl)-1-phenylethene 
• 7601-90-3 perchloric acid 
• 64-19-7 acetic acid 
• 7446-70-0 aluminium trichloride 
• 7664-93-9 sulfuric acid 
• 7664-39-3 hydrogen fluoride 
• 7637-07-2 boron trifluoride 

Downstream Products

• 7615-23-8 2-(4-(1-phenylethyl)phenoxy)ethanol 
• 33314-03-3 butyl-[4-(1-phenyl-ethyl)-phenyl]-ether 
• 4237-44-9 2-(1-phenylethyl)phenol 
• 94676-11-6 1-acetoxy-4-(1-phenyl-ethyl)-benzene 
• 92291-64-0 2,6-dichloro-4-(1-phenyl-ethyl)-phenol 
• 85243-22-7 Benzoesaeure-<4-(1-phenyl-ethyl)-phenylester> 
• 104307-29-1 [4-(1-phenyl-ethyl)-phenyl]-propyl ether 
• 1955-98-2 [4-(1-phenyl-ethyl)-phenoxy]-acetic acid 
• 93902-87-5 1-butyryloxy-4-(1-phenyl-ethyl)-benzene 
• 79628-43-6 potassium 2,6-dinitro-4-(1-phenylethyl)phenoxide 
• 62737-76-2 2-tert-Butyl-4-(1-phenyl-ethyl)-phenol 
• 62737-77-3 2-Cyclohexyl-4-(1-phenyl-ethyl)-phenol 
• 53718-32-4 1,3,3-trimethyl-1-phenylindan-5-ol 
• 1029-77-2 1-Phenyl-1-(4-trimethylsiloxy)-phenylaethan 

Relevant academic research and scientific papers

Phosphorous acid-catalyzed alkylation of phenols with alkenes

A H3PO3-catalyzed alkylation of phenols with alkenes is achieved in a facile, efficient, and selective manner. The reaction shows a unique selectivity, i.e., excellent regioselectivity, thorough suppression of overalkylation, without alkylation of a simple phenyl ring, and can selectively provide ortho-, meta-, or para-alkylated phenol derivatives in good to excellent yields. This feature along with mild reaction conditions, sensitive functional group tolerance, and scale-up synthesis and late modification of phenolic bioactive compounds make it an ideal and practical alternative for the modification of phenols.

New approach to the generation of aryldifluoroboranes–prospective acid catalysts of organic reactions

A new approach for preparation of aromatic and fluoroaromatic difluoroboranes via the interaction between corresponding aryltrifluoroborates and ionic liquids containing tetrachloroaluminate-anion and aluminum chloride has been developed. Catalytic properties of obtained aryldifluoroboranes have been investigated in model reactions of phenols alkylation. The dependence of catalytic properties on both the nature of solvent used and the type of substituents in the aromatic ring of difluoroborane has been established.[Figure presented]

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Efficient catalyst for hydroarylation reaction of styrene with phenol to obtain high DSP selectivity in mild condition

Background: Technical mixture of styrenated phenols including mono-, di-, and tristyrenated phenol, has been commonly applied for industrial materials such as rubber or plastic stabilizer, antioxidant, and nonionic surfactant, etc. Among these styrenated phenols, di-styrenated phenol should be most effective as rubber and plastic stabilizers. Although a number of catalysts for the synthesis of styrenated phenols have been explored, researches on the synthesis of styrenated phenol generally have been focused on selective preparation of mono-styrenated phenol MSP, rather than distyrenated phenol DSP. In this paper, we have investigated the hydroarylation reaction of styrene with phenol to find the optimal catalyst, including single catalysts and mixed catalysts, to get high selectivity to DSP under mild reaction conditions. Method: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. To optimize the reaction conditions, hydroarylation reactions of styrene with phenol employing InCl3 catalyst were carried out with a variety of styrene amount, catalyst amount, reaction time, and reaction temperature. Halogenpromoted hydroarylation reactions of styrene with phenol were investigated in the presence of NBS or I2 as a halogen source and a variety of metal halides as a Lewis acid catalyst. Br-promoted hydroarylation reactions of styrene with phenol were accomplished using InCl3 along with NBS under a variety of NBS amount and reaction temperature. To explore the scope of Br-promoted hydroarylation, the reactions of various styrene derivatives with phenol were carried out using NBS and InCl3. Results: Hydroarylation reactions of styrene with phenol using various single catalysts, such as inorganic acids, organic acids, Lewis acids, and metal salt catalysts, have been conducted. Among 19 catalysts used, best results in both high conversion of phenol and high DSP selectivity are obtained with InCl3 catalyst. Using InCl3, total yield of styrenated phenols is 98% and product selectivity MSP/DSP/ TSP is 20/65/13. When InCl3 as an optimal catalyst was applied for the hydroarylation reactions of styrene with phenol under various reaction conditions, the optimal reaction conditions for obtaining a high yield, high DSP, and low MSP are as follows: styrene/phenol = 2 molar ratio, catalyst/phenol = 0.1 molar ratio, reaction time 6 hours, reaction temperature 120°C. In the halogen-promoted hydroarylation reactions of styrene with phenol in the presence of NBS or I2 as a halogen source and various metal halides as a Lewis acid catalyst, best yield (99%) and DSP selectivity (MSP/DSP/ TSP=13/42/41) were obtained using NBS and InCl3. The optimal reaction condition for Br-promoted hydroarylation reaction was found to be phenol 1 eq., styrene 2 eq., InCl3 0.04 eq., NBS 1 eq., 4 hours reaction time, room temperature. For the reactions of various styrene derivatives with phenol using NBS and InCl3, the best DSP selectivity was observed for the CH3-substituted styrene derivative. Conclusion: We have developed hydroarylation reaction of styrene with phenol for obtaining a high yield and a high DSP selectivity even at room temperature. Using NBS as a Br source and InCl3 as a catalyst at room temperature, Br-promoted hydroarylation reaction of styrene with phenol yields good results with respect to both yield and DSP selectivity.

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING ZIRCONIUM OXIDE SOLID ACID CATALYST MANUFACTURED BY BEING IMPREGNATED ZIRCONIUM HYDROXIDE IN SULFURIC ACID AQUEOUS SOLUTION

The present invention relates to a selective preparation method of di-styrenated phenol represented by chemical formula 1 obtained by making a phenol compound represented by chemical formula 2 react with a styrene monomer in the presence of a zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with an aqueous sulfuric acid solution. In chemical formulas 1 and 2, R_1 and R_2 are each independently selected from hydrogen, a C_1-C_20 alkyl group, a C_1-C_20 alkoxyl group, a C_3-C_30 cycloalkyl group, and a C_6-C_30 aryl group. The selective preparation method according to the present invention can minimize the amount of an unreacted residual material and can dramatically increase selectivity of di-styrenated phenol by exhibiting a high reactivity in the presence of the zirconium oxide solid acid catalyst prepared by impregnating zirconium hydroxide with the aqueous sulfuric acid solution.COPYRIGHT KIPO 2018

METHOD OF PREPARING FOR SELECTIVE DI-STYRENATED PHENOL USING TITANIUM DIOXIDE SOLID ACID CATALYST

The present invention relates to a method for producing di-styrenated phenol. More specifically, the present invention relates to a method for selectively producing di-styrenated phenol at high yield using solid titanium dioxide acid catalyst. According to the present invention, since the method for producing di-styrenated phenol ensures high reactivity in the presence of solid titanium dioxide acid catalyst, the method for producing di-styrenated phenol can minimize an amount of unreacted residues while remarkably increasing selectivity of di-styrenated phenol.(AA) Titanium dioxide (Powder form, 20 g)(BB) Titanium dioxide + Sulfuric acid + Distilled water (500 ml)(CC) Stir (Room temperature and 3 hours)(DD) Dry (110anddeg;C, and 12 hours)(EE) Sintering (600anddeg;C, 2 hours, and air atmosphere)(FF) Titanium dioxide solid acid catalyst (SO_4^2-/TiO_2) (Sulfuric acid : 5 wt%)COPYRIGHT KIPO 2017

METHOD FOR MANUFACTURING STYRENATED PHENOL

The present invention relates to a method for producing styrenated phenol which is represented by chemical formula 1. According to an embodiment of the present invention, provided is a method for producing styrenated phenol, which comprises the following steps: a step (a) for carrying out a reaction between a phenol compound and a styrene compound in the presence of a first acid catalyst; and a step (b) for carrying out a reaction after additionally inserting a styrene compound into a product obtained in the step (A) in the presence of a second acid catalyst. In the chemical formula 1, n refers to an integer of 1-3.COPYRIGHT KIPO 2017

Synthesis and catalytic reactivity of mononuclear substituted tetramethylcyclopentadienyl molybdenum carbonyl complexes

The reactions of five dinuclear carbonyl complexes [(η 5-C5Me4R)Mo(CO)3]2 [R = allyl, n Bu, t Bu, Ph, Bz] with I2 in chloroform solution gave the corresponding mononuclear substituted tetramethylcyclopentadienyl molybdenum carbonyl complexes [(η 5-C5Me4R)MoI(CO)3] [R = allyl (1), n Bu (2), t Bu (3), Ph (4), Bz (5)]. The molecular structures of complexes 2, 3 and 5 were determined by X-ray diffraction analysis. The results show that the substituent in the ring can directly affect the Mo-I bond distances; the more sterically hindered the substituent, the longer the Mo-I bond. Friedel-Crafts reactions of aromatic compounds with a variety of alkylation reagents catalyzed by the complexes showed that all of these mononuclear molybdenum carbonyl complexes have catalytic activity in Friedel-Crafts alkylation reactions. Indeed, compared with traditional catalysts, these mononuclear metal carbonyl complexes have obvious advantages such as higher activities, mild reaction conditions, high selectivity, simple post-processing, and environmentally friendly chemistry.

STYRENATED PHENOLIC COMPOSITION, AND PRODUCTION METHOD THEREFOR

PROBLEM TO BE SOLVED: To provide a styrenated phenolic composition having high content of tristyrenated phenolic compound and low content of impurities such as a styrene oligomer, and a production method therefor. SOLUTION: There are provided the styrenated phenolic composition containing a specific monostyrenated phenolic compound, a specific distyrenated phenolic compound and a specific tristyrenated phenolic compound and the production method for the styrenated phenolic composition. The styrenated phenolic compound has total content of the monostyrenated phenolic compound, the distyrenated phenolic compound and tristyrenated phenolic compound of 98 mass% or more per 100 mass% of an organic product. The content of the tristyrenated phenolic compound in the styrenated phenolic composition is 80 mass% or more and the content of accessory components is 2 mass% or less including 0. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

Microwave-assisted hydroarylation of styrenes catalysed by transition metal oxide nanoparticles supported on mesoporous aluminosilicates

Abstract The addition of phenols to styrene to form ortho and para-(1-phenylethyl) phenols was catalysed by a range of metal oxide nanoparticles supported on mesoporous aluminosilicates (M/Al-SBA-15 catalysts) under microwave irradiation. Moderate to excellent yields to products could be obtained at short times of reaction (typically 10 min). 0.5%Fe/Al-SBA-15 as readily available, environmentally friendly and cheap catalysts exhibited remarkable improvements in yield as compared to the majority of utilized catalysts. The heterogeneous catalyst can be reused at least three times without a significant loss in activity.