Phenyl Carbinol

The condensation of thiophene with ketones, under the influence of 70% H2SO4, leads to di-2-thienylmethane derivatives. With acetone, 2,2-di-(2-thienyl) propane (97) is obtained. The condensation of thiophene with dimethyl phenyl carbinol, methyl diphenyl carbinol, and f-butylalcohol, in the presence of SnCU gave (98), (99), and 2,5-di-f-butylthiophene, respectively. Triphenyl carbinol does not... 

B.Bg (0.15 mol) of 4-phenylbenzophenoneare dissolved in 200 ml of ethanol and 3 g (0.075 mol) of sodium borohydride are added. After heating for 15 hours under reflux, and allowing to cool, the reaction mixture is hydrolyzed with water containing a little hydrochloric acid. The solid thereby produced is purified by recrystallization from ethanol, 36 g (B9% of theory) of (biphenyl-4-yl)-phenyl-carbinol [alternatively named as diphenyl-phenyl carblnol or a-(biphenyl-4-yl)benzylalcohol] of melting point 72°-73°C are obtained. 

CL-Phenylethanol (a-Phenylethyl alcohol, Methyl-phenyl carbinol). C6H5, CHOH.CH3, mw 122.16, liq, bp 203.6° at 475mm, d 1.019g/cc at 13/4°. Prepn and other properties are given in Beil 6,475, (236) [445]... 

CI-C6H4-C0-C6H5 (4 -Chlor-ph enyl) -phenyl-carbinol 78 ... 

Synonyms AI3-01680 Benzal alcohol Benzene carbinol Benzene methanol Benzoyl alcohol Benzylicum BRN 0878307 Caswell No. 081F CCRIS 2081 EINECS 202-859-9 EPA pesticide chemical code 009502 Elydroxymethylbenzene a-Elydroxytoluene NC1-C06111 NSC 8044 Phenol carbinol Phenyl carbinol Phenyl methanol Phenyl methyl alcohol a-Toluenol UN 2810. 

Phenylbutane, see sec-Butylbenzene Phenyl carbinol, see Benzyl alcohol Phenylcarboxylic acid, see Benzoic acid Phenyl chloride, see Chlorobenzene... 

Reaction of telluronium salts/n-BuLi with carbonyl compounds synthesis of alcohols with telluronium salt (a2) (typical procedure) A solution of n-BuLi (1.1 mmol) in hexane is added to a solution of the telluronium salt (0.459 g, 1.2 mmol) in THF (6 mL) at -78°C under N2. The mixture is warmed at -60°C and stirred for 10 min. After cooling again at -78°C, p-chlorobenzaldehyde (0.140 g, 1.0 mmol) in THF (2 mL) is added. The mixture is then allowed to warm at room temperature. After the reaction is complete (monitored by TLC), the usual work-up and flash chromatography yield pure p-chlorophenyl(phenyl)carbinol. 

A number of observations have been made which qualitatively suggest that carbonium ions adjacent to metallocene systems possess unusual stability. Ferro-cenecarboxaldehyde, for example, is soluble in dilute hydrochloric acid (5), ferrocenyl carbinols such as ferrocenyl phenyl carbinol form ethers with great ease (124), and ferrocenylmethylcarbinol can be dehydrated to vinylferrocene under exceedingly mild conditions (114). The concept of stabilizations of this type has also been used to explain certain anomalous ring substitution reactions. 

To give an impression of the nature of useful experimental results, some flow birefringence measurements which were obtained on a solution of polystyrene in methyl 4-bromo-phenyl carbinol, are reproduced in Figs. 1.2 and 1.3. The concentration of the solution was 2 wt. percents, measuring temperatures are indicated in the figures. The special polystyrene used was a well-known sample of anionically polymerized polystyrene, viz. S 111, provided by the courtesy of Dow Chem. Corp. Its molecular weight is 224,000. The indicated solvent is, at 18 °C, a 0-solvent and possesses practically the same refractive index as polystyrene itself (32). The measurement results are kindly provided by Daum from his still unpublished work. 

Fig. 1.2. Extinction angles % vs. shear rate q for a 2 wt. per cent solution of anionic polystyrene Sill in methyl 4-bromo-phenyl carbinol at the indicated temperatures...

Fig. 1.4 gives such a plot, which was prepared by Philippoff (8,9) from his early measurements on a 15 per cent solution of polyisobutylene (P-100) in decalin (measurement temperatures 30 and 50°C). From this figure it is clearly seen that An as a function of p21 is non-linear. In contrast to the above mentioned solution of S 111 in methyl 4-bromo-phenyl carbinol, the solution of the poly-isobutylene P-100 in decalin does not form a second order fluid. However, for the product A n sin 2%, one obtains a beautiful straight line. The stress-optical law seems to hold also for this more general type of fluid. ... 

Fig. 3.2. Reduced stored free energy Fa vs. reduced shear stress / for a 0.57 wt. per cent solution of Taps. No. 5 in methyl (4-bromo-phenyl) carbinol at various temperatures, viz. ( ) 18°, ( ) 30°, (a) 40° and (A) 50° C (32)...

The data quoted in these figures were obtained on solutions of Taps. No. 5 and S 111 in methyl (4-bromo-phenyl) carbinol. The 0-temperature of these systems is 18° C. In Table 3.2 the intrinsic viscosities of both samples are quoted for four temperatures. The solvent viscosities and densities are given in the lowest two rows. 

This is very remarkable in view of the enormous difference of intrinsic viscosities in methyl (4-bromo-phenyl) carbinol and in bromo-benzene. 

Fig. 3.4. Extrapolation of reduced steady state compliance /, jjto zero concentration for solutions of Sill in methyl (4-bromo-phenyl) carbinol (32). The indicated errors are obtained from all measurements together, irrespective of measurement...

Fig. 4.4. Concentration dependence of reduced steady-state shear compliance J,B for a series of anionic polystyrenes, as mostly provided by Pressure Chem. Corp., Pittsburgh, Pa. Except for the solutions of the three lowest concentrations of S 111 (Dow Chem. Corp.), which were prepared with methyl (4-bromo-phenyl) carbinol and used at various temperatures, all solutions were prepared with mono-bromo-benzene and used at 25° C (32). Measurement temperatures for the melts varied from 196 to 240° C (59). For the molecular weights of the polymers see Table 4.1...

Fig. 5.9. Comparison of extinction angle curves of high molecular weight fractions of polystyrene and cellulose tricarbanilate, using linear scales and reduced shear rate For data on polystyrene Taps. No. 5 and solvents see Table 3.2. (n) Taps. No. 5 in methyl (4-bromo-phenyl carbinol) at 18° C (theta-temperature), (V) the same at 50° C, (o) Taps. No. 5 in monobromo benzene at 25° C, ( ) cellulose tricarbanilate M = 720,000 in benzophenone at 55° C (jy = 4.70 cps) and (a) at...

Acetyl chloride acephate, azaconazole, chlorfenvinphos, cyhalotrin, dimethomorph, dinoseb acetate, fenitropan, fluxofenim, furconazole, mefluidide, propiconazole Acetyl chloride (dichloro) see dichloro Acetyl chloride phenyl carbinol bromadiolone Acetylene aldrin, 2,4 DB Acetyl hydrazine metamitron Acetylide (sodium) pronamide Acetyl magnesiun bromide empenthrin Acetyl morpholine dimethomorph Acetyloxy propionaldehyde furmecyclox Acrolein 8 hydroxy quinoline sulfate Acrylic acid propaquizafop Acryloyl chloride propaquizafop Acrylonitrile fenpiclonil, fludioxonil, nipyraclofen Aldrin dieldrin, endrin... 

Methyl phenol see p-Cresol Methyl phenyl carbinol crotoxyphos Methyl phenyl glyoxalate metamitron... 

Styrene is also produced as coproduct from a PO process. In this route, EB is oxidized to its hydroperoxide and reacted with propylene to yield propylene oxide. The coproduct methyl phenyl carbinol is then dehydrated to styrene. For every pound of PO produced, up to 2.5 lb of styrene can be produced. In 2000, about 25 percent of styrene was produced by this process in the United States. 

The relative configuration of cynometrine and isocynometrine were determined by X-ray diffraction analysis. The absolute configuration of the phenyl carbinol chiral center was determined by the method of Horeau and Kagan (154). From UV spectroscopic data and the rotations of the different alkaloids and their derivatives, the steric structures 94-102 have been deduced as depicted in the illustrations (155). 

Methylation of the lactam nitrogen and condensation with methyl benzoate in the presence of lithium diethylamide in THF afforded a ketone, which, on sodium borohydride reduction, yielded racemic isocynometrine (99) as the major component of a mixture of two epimeric phenyl carbinols (Scheme 8) (155). Racemic anantine (94) and cynometrine (95) have been synthesized analogously, starting from 4-formyl- 1-methylimidazole (155). 

---