Benzyl-phenol

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... 

As seen in the retro-synthetic Scheme 5.3, intermediate 15 is useful for both routes. The choice of benzyl protection group was made based on the robust stability of benzyl phenol ethers toward most reactions and several possible avenues to remove it, although it was reported from Medicinal Chemistry that benzyl group removal via hydrogenolysis posed challenges in this compound. The choice of iodide substitution was born out of the known high reactivity of iodides in the Ullmann-type coupling reaction with alcohols and the robust stability of aryl iodides in many other common reactions. 

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. 

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%). 

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

Shen and Ii [149] extracted caesium (and rubidium) from brine samples with 4-tert-butyl-2-(a methyl-benzyl) phenol prior to atomic absorption spec-trometric determination of the metal. 

Caesium Cs complexed with 4-tetrabutyl-2(a-methyl benzyl) phenol and solvent extracted AAS [149]... 

A recent X-ray determination of the structure of the 2-benzyl phenol derivative [H2Os3(CO)9(OC6H3CH2Ph)] indicates a different bonding mode from that in Fig. 33a, with a switch in the nature of the bonding groups between bridging and terminal roles (181). Detailed analysis of the X-ray data favors the structure form in Fig. 34a, although attempts to identify chemically the diene character were not successful. This structure does throw some doubt on the nature of the related aniline complex. 

With phenols either the phenolic nr nuclear hydrogens can react lo give benzylaryl ether or benzylated phenols. Reaction with NaCN gives benzyl cyanide (phenylacelonitrile) with aliphatic primary amines the product is (he N-alkylbenzylamine. and with aromatic primary amines N-benzylaniline is formed. Benzyl chloride is converted 10 butyl benzyl phlhalatc plasticizer and other chemicals. 

Benzyl Phenol 1322-51-6 Butyl Acetyl Ricinoleate 140-04-5 Calcium Bromide 7789-41-5... 

Creaylol—Cresof—Cresylie acid—Benzylic phenol—Cresylic p/tenof— C H (GH,)OH—198—aceompames phenol in coal- and wo -U, from wbicQ it may be obtained by fractional distiUaticn it is more readily obtained pure from toluene. 

Synonyms 4-Cumylphenol p-Cumylphenol p-(a-Cumyl) phenol p-(a,a-Di methyl benzyl) phenol 4-(Dimethylphenylmethyl) phenol 4-Hydroxydiphenyldimethylmethane 4-(1-Methyl-1-phenethyl) phenol Phenol, p-(a,a-dimethylbenzyl) Phenol, 4-(1-methyl-1-phenethyl)- 4-(2-Phenylisopropyl) phenol Empirical CisHieO Formula C6HsC(CH3)2C6H40H Properties Wh. to tan crystals, phenol odor m.w. 212.29 dens. 1.115 g/ml (25 C) m.p. 74-76 C b.p. 335 C f.p. 72 C flash pt. 320 F Toxicology LD50 (oral, frog) 335 mg/kg poison by ing. irritant TSCA listed Precaution Combustible Hazardous Decomp. Prods. Heated to decomp., emits acrid smoke and irritating vapors Uses Intermediate for resins, insecticides, lubricants, surfactants chain terminator for PC... 

The acid-catalysed rearrangement of benzyl phenolic ethers to diphenylmethane compounds and the rates of rearrangement of (Z)-aryUiydrazones of 5-amino-3-benzoyl-l,2,4-oxadiazole into (2-aryl-5-phenyl-2H-l,2,3-triazol-4-yl)ureas have been reported. ... 

Halogenation of phenol also leads to phenol derivatives which are much more effective than the starting substance. At the same time, the dissociation constant increases with an increase in the number of halogen atoms, i.e. the acidic character of the phenol derivatives becomes more distinctive. The combination of alkylation and halogenation (the latter with preference in the p-position) has led to microbicides which have attained great practical significance as substances for the protection of materials and disinfection, e.g. p-chloro-o-benzyl phenol, p-chloro-m-cresol, p-chloro-/M-xylenol. 

Fig. 29. Decrease in concentration of phenolics in activated sludge (Paulus Genth, 1983). (OPP, u-phenyl-phenol PCMC, p-chloro-m-cresol BP, benzyl-phenol CBP, p-chloro- -benzyl-phenol DC, (2,2 -dihydroxy-5,5 dichloro-)diphenyl methane PCMX, / -chloro-m-xylenol PCP, pentachlorophenol.)...

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