Phenol phenyl benzyl ether

Lithium diphenyphosphide (THF, 25°, 2 h HCl, H2O, 87% yield) selectively cleaves an aryl methyl ether in the presence of an ethyl ether.It also cleaves a phenyl benzyl ether and a phenyl allyl ether to phenol in 88% and 78% yield, respectively. ... 

It also cleaves a phenyl benzyl ether and a phenyl allyl ether to the phenol in 88% and 78% yield, respectively. ... 

Phenyl benzyl ether 320 30 31.4 PhCH3 55, PhOH 50, Benzyl phenol 40... 

Phenyl benzyl ether was mostly converted to toluene and phenol, but partly isomerized to benzyl phenol. 

Furthermore, we studied the effect of phenolic compounds on the thermolysis of phenyl benzyl ether at 320°C, because even reactive phenols such as p-methoxy phenol are quite stable at this temperature. 

As shown in Table IV, all phenols tested were confirmed to accelerate the conversion of phenyl benzyl ether. In this thermolysis, benzyl phenyl ether was decomposed to toluene and phenol (ca. 60%) and also isomerized to benzyl phenol (ca. 40%). 

TABLE IV EFFECT OF PHENOLS ON THE THERMAL DECOMPOSITION OF PHENYL BENZYL ETHER AT 320°C FOR 30 MIN (Phenyl benzyl ether 27 mmole, Tetralin 220 mmole, Additive 140 mmole)... 

Phenyl benzyl ether 400 30 100 PhCH3 61, PhOH 66, PhCH2Ph 6, Benzyl phenol 27, Benzyltetralin 2... 

Photolyses of 31-34 in homogeneous solution results in the formation of diphylethanes 39 (5-15%), phenols 38 (5-15%), ortho-hydroxyphenone 36 (40-60%), and para-hydroxyphenones 37 (20-25%). Small amounts of phenyl benzyl ether 35 (3-8%) were also detected. However, photolyses of all of the four esters on NaY zeolite and Nafion only produce ortho rearrangement products 36. Molecular models suggest that esters 31-34 can enter into NaY zeolite internal surface and the inverse micelle of Nafion. We believe that the preference for formation of ort/zo-hydroxyphenones 36 in the products is a consequence of the restriction on diffusional and rotational motion of the geminate radical pair. 

Alkyl and benzyl aryl ethers undergo acid-catalysed rearrangement to afford phenols. For instance, benzyl phenyl ether under treatment with AlBrs in dichloromethane yields exclusively 2-benzylphenol with simultaneous production of phenol. The ratio of phenol and 2-benzylphenol is hardly affected by the solvent. Other type of catalysts have also been used successfully in this type of rearrangement. For instance, trifluoroacetic acid converts 4-(2 -methyl-but-2 -yl)phenyl benzyl ether (205) to the corresponding phenol 206 (equation 136) and over montmorillonite clays, benzyl phenyl ether (207), is converted to 2-benzylphenol (208) (equation 137) . 

Alkyl aryl ethers are qnite stable on heating. Phenyl benzyl ether isomerizes slowly at 250 °C to afford 4-benzylphenol and its ortho-i ovasc as a minor prodnct" . The conditions of isomerizations of O-aUcylated and O-aralkylated phenols were reviewed . 

Synonyms Agerite alba monobenzone 4-(phenylmethoxy)phenol p-(benzyloxy)phenol hydroquinone benzyl ether p-hydroxy-phenyl benzyl ether benzyl hydroquinone monobenzyl hydroquinone Depigman Pigmex Benzoquin PBP Benoquin Uses antidegradant added to rubber products inhibitor in acrylic resins A... 

The nanospace of zeolite may impose a restriction on the rotational and translational motions of substrate molecules and reaction intermediates. This would promote or discourage specific reactions. The photochemical reaction of phenyl phenylacetates 1-4 (Scheme 10.25) within zeolites can be regarded as a good example [110, 111]. Photolysis of 1-4 in a homogeneous solution results in the formation of ortho-hydroxyphenones (40-60%), para-hydroxyphenones (20-25%), phenols (5-15%), diphylethanes (5-15%), and phenyl benzyl ethers (3-8%). However, the photolysis of all four esters in NaY zeolite can produce only ortho-hydroxyphenones. Molecular models suggest that the esters 16-19 can enter into... 

Tarbell and Petropoulos159 measured the rate of formation of phenol from benzyl phenyl ether catalysed by aluminium bromide and found it to be a first-order process. Moreover, the rate coefficient was the same as that for the formation of phenol from ortho benzyl phenol. Since the ratio of products (phenol ortho benzyl phenol) was unaffected by a large change in the temperature it was argued... 

Cleavage conditions for alkyl benzyl ethers prepared from acid-labile benzyl alcohols are similar to those for the corresponding benzyl esters (Table 3.30). Aryl benzyl ethers, however, are generally cleaved more easily by acidolysis than esters or alkyl ethers. Phenols etherified with hydroxymethyl polystyrene, for instance, can even be released by treatment with TFA (Entry 1, Table 3.31). It has also been shown that Wang resin derived phenyl ethers are less stable than Wang resin derived esters towards refluxing acetic acid [29]. Alternatively, boron tribromide may be used to cleave aryl ethers from hydroxymethyl polystyrene [573],... 

Previous studies of the reactions of guaiacol (orthomethoxy-phenol) (3 ), dibenzyl ether (4 ), and benzyl phenyl amine (5) in dense water elucidated parallel hydrolysis and pyrolysis pathways, the selectivity to the latter increasing with water density. Reactant decomposition kinetics were interestingly nonlinear in water density and consistent with two mechanistic interpretations. The first involved "cage" effects, as described for reactions in liquid solutions (6 ). The second led to parallel pyrolysis and solvolysis reaction pathways wherein associated rate constants were dependent upon pressure. These two schemes are probed herein through the reactions of benzyl phenyl amine (BPA) in water and methanol. 

Both of these compounds yield sulphides or thio-ethers. Thio-phenol by the diazo reaction yields di-phenyl sulphide, CeHs—S—Cell5, di-phenyl thio-ether and benzyl mercaptan yields di-benzyl sulphide, CeHs—CH2—S—CH2—CeHs, di-benzyl thio-ether. These sulphides on oxidation yield sulphones (p. 526). 

Relatively little basic information has been published regarding the kinetics of phenol-formaldehyde intermediates, especially of phenols, methylol phenols, benzyl alcohol and benzylic ethers with isocyanates. Due to the fact that a typical resole contains both phenolic and benzylic hydroxyl groups, it was of interest to determine their reactivity toward isocyanates in the presence of various catalysts, as well as the effect of substitution on their reactivity. This investigation describes the kinetics of model phenols and model benzyl alcohols with phenyl isocyanate catalyzed with either a tertiary amine (dimethylcyclo-hexylamine, DMCHA) or an organotin catalyst, dibutyltin dilaurate (DBTDL) in either dioxane or dimethylformamide solution. 

Commercially supplied analytical grade substrates, benzyl ether, N-phenyl ben-zylamine and 4-(benzyloxy) phenol and the solvents (tetrahydrofuran, methanol, octanol, cyclohexane, acetone and methyl ethyl ketone) were used in this study. 

Amino-6-ethoxybenzothiazole C9HioN402S2 Sulfamethizole C9H10O 2-Ally I phenol Cinnamyl alcohol 2,4-Di methyl benzal dehyde p-Ethylbenzaldehyde Ethyl phenyl ketone Hydrocinnamaldehyde 4 -Methyl acetophenone 2-Phenyl propanal Propiophenone p-Tolylacetaldehyde C9H10O2 Acetanisole Benzyl acetate m-Cresyl acetate o-Cresyl acetate p-Cresyl acetate p-Ethoxybenzaldehyde Ethyl benzoate Hydrocinnamic acid 2-M ethoxy-4-vi nyl phenol a-Methylbenzyl formate Methyl phenylacetate Methyl p-toluate Phenethyl formate Phenyl glycidyl ether... 

Formaldehyde, glyoxal, glutaraldehyde, polyaldehyde (polyacrolein), aldehyde-amine condensation products, aldehyde-glycol condensation products, bronopol o-Phenyl phenol, o-benzyl-jn-chlorophenol,p-chloro-m-xylenol, o, p, p -trichloro-o -hydroxydiphenyl ether (Triclosan) Nonylphenoxypoly(ethyleneoxy) ethanol-iodine complex, ethoxylated nonyl phenol-iodine complex, polyvinyl pyrrolidone-iodine complex... 

Phenol cmtinued) Cumene Mesitylene Propylbenzene Pseudocumene Benzyl ethyl ether Phenyl propyl ether N, N-Dimethyl-o-toluidine Phorone... 

PMR spectroscopy has been applied to the characterisation of a wide range of homopolymers including PMMA [286-289], PVC [290-294], PS [293, 295, 296], polyvinyl ethers [297-300], polyacrylic acid [301], poly(methyl-a-chloroacrylate) [302], carboxy terminated polybutadiene [303], poly(a-methyl styrene) [304], natural rubber [305-307], chlorinated polyisobutylenes [308], sulfonated PS resins [309, 310], polyvinyl phenyl ether [311], lactone polyester [312], chlorinated PVC [313], PC [314], poly 1,3 butadiene [315], poly-2-allyl phenyl acrylate [316], poly(4-methyl-pentene-1) [317], polymethacrylic acid [318], PP [296], cyclic ethers [319], polymethacrylonitrile [320], poly(a-methyl styrene) tetramer [321], PEG [322], PE [289], polyacrylamide [311], polymethylacrylamide [323], polypyrrolidone [324], polychloroprene [325], phenol formaldehyde resins [326, 327], Nylon 66 [328], polyvinylidene fluoride [329], polyvinyl formate [330], polyacrylonitrile [331], epoxy resins [332], allyl biguanide [333], poly(2-isopropyl-2-oxazollines) [334] and trehalose vinyl benzyl ether [335]. 

How could you prepare benzyl phenyl ether from benzene and phenol More than one step is required. 

In some model compound studies with the i-PrOH/KOH system we found that anthracene was converted to 9,10-dihydroanthracene in 64% yield. Benzyl phenyl ether was also studied and was converted to a polymeric material under the reaction conditions. There were no traces of phenol nor toluene, the expected reduction products. 

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