1 - 4- -4-tolyl-phenyl methanol

Analytical Properties Resolution of such compounds as racemic 1,2-diphenol-ethanol, 2,2 -dihydroxyl-1, 1 -dinaphthyl, 2,3-diphenyloxirane, and phenyl-2-pyrid-o-tolyl-1-methanol Reference 38... 

Mandereau et a/.193 prepared the alcohol (133) by reducing ethyl 2-pyridylaminopropionate with lithium aluminum hydride. The alcohol was then transformed with thionyl chloride to the chloride (134) and cyclized with an equimolar amount of sodium hydroxide in methanol to the pyrido-[l,2-u]pyrimidine (135). The 4-phenyl and 4-(p-tolyl) analogs were prepared in a similar fashion. The 4-(p-methoxyphenyl) derivative could only be obtained by heating the alcohol of type 133 in acetic anhydride. The pyrido[l,2-a]pyrimidine-4-carboxylicacid (137) was prepared by ring transformation of the pyridylpyrrolidinone (136) with methanolic sodium hydroxide.193... 

For example, in the optical resolution of diltiazem, a benzothiazepin derivative, with optically active mandelic acid, one of the diastereomeric salts with the same stereochemical sign (+) (+) or (-) (-) is crystallized from ethyl acetate whereas another with the opposite stereochemical sign (+) ( ) or (-) (+) is obtained from a mixed solvent of ethyl acetate and benzene (1 1).21 In the resolution of 1-phenyl-2-(p-tolyl)ethylamine with the same chiral acid, the same sign salt crystallizes from 50 % aqueous methanol and the opposite one from 2-propanol.22... 

Most of the compounds are readily soluble in water and in pyridine, slightly soluble.in methanol and in ethanol (which are the usual recrystallizing solvents), and sparingly soluble in ether, acetone, light petroleum, chloroform, benzene, and ethyl acetate. AT-Phenyl- and W-p-tolyl-D-manno-sylamine, like n-mannose phenylhydrazone, have unusually low solubilities. 

The preparation of crystalline methyl ethers of iV-phenyl- or Af-p-tolyl-aldosylamine by condensation of aniline or p-toluidine with aldose methyl ethers proceeds, in many cases, readily and quantitatively in methanolic or ethanolic solution, either at room or reflux temperature. For this reason, such derivatives are frequently used to characterize aldose methyl ethers isolated during constitutional studies on polysaccharides. For D-glucose, for example, crystalline 2-0-methyl-, 6-0-methyl-,3,4-di-O-methyl-, 2,3,4-tri-O-methyl-, 2,4,6-tri-O-methyl-, " and 2,3,4,6-tetra-O-methyl-A-phenyl-n-glucosylamine have been prepared in this way. Although anomeric forms of A -arylaldosylamine methyl ethers are possible, such anomeric pairs have not been isolated. No similar derivatives have been obtained from ketose methyl ethers. 

The following examples illustrate different aspects of Scheme 1 in operation. p-Chlorophenyl azide, malononitrile, and methanolic sodium methoxide, set aside, gave 4-amino-5-cyano-3-p-chlorophenyltriazole (rC, 1 hr, 98%) (60CB2001). Methanolic sodium methoxide was added dropwise to a mixture of p-tolyl azide and phenylacetonitrile (benzyl cyanide) next day, the temperature was raised to 25°C, and the preparation set aside for 10 hr, giving 4-amino-5-phenyl-3-p-tolyltriazole (92%) (57JOC654). 

In the case of unsyimnetrical diaryliodonium salts (the anisyl, tolyl or nitrophenyl derivatives of phenyliodonium salts - or some thienyl aiyliodonium salts ), the product composition is always in favour of the ligand coupling product involving the less electron-rich arene group. A good yield of 3-methoxyindole (60%) was obtained in the reaction of phenyl 3-indolyliodonium chloride with methanol in the presence of boron trifluoride-etherate. ... 

Nine organomercury compounds (e.g., methyl-, methoxyethyl-, phenyl-, tolyl-and benzoyl-mercury nitromersol and mersalylic acid) were baseline resolved on a C g column (A = 230nm) using a 25min 30/70 -y 50/50 methanol/water (50 mM ammonium acetate buffer at pH 5.0 with 0.1 mM 2-mercaptoethanol) gradient [147]. Note that the mercaptoethanol has a strong stench and so the system should be located in a well-ventilated area. Detection limits fi om 7 to 95 pg/L were reported (analyte dependent). 

Prompted by earlier results which indicated that the rate law for substitution of Cl in square-planar rran -[Pt(PEt3)2(R)Cl] (R = phenyl, jp-tolyl, or mesityl) complexes included an associative as well as the normal dissociative path only in the case of substitution by strong biphilic ligands (e.g. CN, SeCN ), Ricevuto et al. have re-examined the reaction with weakly nucleophilic pyridine in methanol ... 

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