Methyl phenyl carbinol

There is an isomeric and closely associated alcohol, phenyl-methyl carbinol, CgH5CH OH)CHg, known to chemists. This is a liquid of different odour, but which is not used very much in synthetic perfumery. It is an oil boiling at 203°, and forms an acetate which is found naturally in essential oil of gardenia. This ester is of use in blending perfumes of this type of flower. 

Phenyl methyl carbinol Acetophenone or ethyl- R A. K salt, H20 — 124(W) 138... 

The synthesis of CHDTC02H is, in principle, straightforward and was first accomplished in two laboratories in 1969 150). A modified version of the Comforth synthesis151) is shown in Fig. 67. Most of the steps are self-evident. The doubly labeled phenyl methyl carbinol is, of course, a dl pair in the first instance the absolute stereochemistry at the CHDTX chiral center is RS but the relative stereochemistry of the two chiral centers is defined as IRS,2RS, i.e. only one of the two possible diastereomers is obtained. The resolution at the methyl group occurs automatically when the carbinol is resolved by classical methods. 

The peroxide processes convert propylene to its epoxide while reducing the hydroperoxide to the corresponding alcohol (e.g., tert-butyl alcohol or phenyl methyl carbinol). Because the processes produce the alcohols in larger amounts than PO, their success depends upon finding uses for the alcohols. tert-Butyl alcohol can be dehydrated to isobutylene and hydrogenated to isobutane for recycle to the PO process. It can also be converted to MTBE. Phenyl methyl carbinol can be dehydrated to styrene, making this process a more involved... 

Mercaptoethanol Phenyl methyl carbinol Diacetone alcohol... 

Percentage Reduced to Carbinol 35.7, as phenyl methyl carbinol 26, as phenyl ethyl carbinol 43, as benzyl isopropyl carbinol 41, as phenyl n-propyl carbinol... 

Isobutanol can be dehydrated to isobutene and used as an intermediate or converted to methyl t-butyl ether, used in unleaded gasoline. Phenyl methyl carbinol can be dehydrated to styrene, and it is a major intermediate for this monomer. 

There exist three isomers of phenyl-propyl alcohol, all of which have been prepared and described, and, although not yet introduced into commerce, may eventually be so. These are as follows Benzyl-methyl-carbinol, CgHj. CHj. CH(OH)CHg, boiling at 215° phenyl-ethyl-carbinol, CgHg. CH(OH)CH2. CHg, boiling at 221° and benzyl-dimethyl-carbinol, C Hg. C(OH)(CHg)2, melting at 21° and boiling at 225°. 

The reaction of crotonaldehyde and methyl vinyl ketone with thiophenol in the presence of anhydrous hydrogen chloride effects conjugate addition of thiophenol as well as acetal formation. The resulting j3-phenylthio thioacetals are converted to 1-phenylthio-and 2-phenylthio-1,3-butadiene, respectively, upon reaction with 2 equivalents of copper(I) trifluoromethanesulfonate (Table I). The copper(I)-induced heterolysis of carbon-sulfur bonds has also been used to effect pinacol-type rearrangements of bis(phenyl-thio)methyl carbinols. Thus the addition of bis(phenyl-thio)methyllithium to ketones and aldehydes followed by copper(I)-induced rearrangement results in a one-carbon ring expansion or chain-insertion transformation which gives a-phenylthio ketones. Monothioketals of 1,4-diketones are cyclized to 2,5-disubstituted furans by the action of copper(I) trifluoromethanesulfonate. ... 

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. 

When cumene hydroperoxide is heated to cumene cracking temperatures, at least partial decomposition probably occurs. Thus, it is desirable to measure the inhibitor action of the decomposition products of cumene hydroperoxide. Some low-temperature thermal decomposition products which were identified (by chemical and mass spectroscopic analyses) are acetophenone, phenyl-dimethyl-carbinol, a-methylstyrene, phenol, acetone, and methyl alcohol. Kharasch, Fono, and Nudenberg (7) obtained similar results. According to them, the chief decomposition products at 158° are acetophenone and phenyl-dimethyl-carbinol, with acetophenone becoming relatively more important at higher temperatures. Since the temperature used for the cracking reaction is above 300°, acetophenone is probably the most important decomposition product. The equilibrium constant for the adsorption of cumene hydroperoxide and some of the individual decomposition products on catalytic sites are included in Table I. 

Carbinol kar-bo- n61, - nol [ISV, fir. obs. Gr Karbin methyl, fir. Gr karb-] (ca. 1885) n. (1) -CH2OH. Monovalent primary alcohol radical. It may be part ofi an aliphatic or an aromatic alcohol. For example, ethyl alcohol (C2H5OH) can be described as methyl carbinol, or benzyl alcohol (C6H5CH2OH) as phenyl carbinol. (2) It is sometimes used as a Syn methanol. 

In certain very limited cases the 750 cm" band shows splitting into a group of weaker bands at the same frequency. This occurs in the cw-forms of phenyl propenyl carbinol and styryl methyl carbinol [37], although the trans forms have only a single band of normal position and intensity. The reasons for this are not known, but it may be connected with steric interferences in the cis-compounds. Benzoyl derivatives also give rise to distortions in this region. The 750 cm" band is not seen in the Raman spectrum and the 690 cm" band appears only weakly. 

Reaction of diclilorocarbene with substituted benzaldehydes affords the corresponding mandelic acids. It might be supposed that this reaction does not involve dichlorocarben but rather its precursor, the trichloromethide ion. Nucleophilic addition of the trichlorc methyl anion to benzaldehyde should yield phenyl trichloromethyl carbinol. In control experiments, however, phenyl trichloromethyl carbinol was not hydrolyzed to mandelic acid under the reaction conditions. It was suggested that the reaction involves dichlorocarbene addition to the benzaldehyde carbonyl to form 2,2-dichloro-3-phenyloxirane followed by rearrangement to a-chlorophenylacetyl chloride which then is hydrolyzed as shown in equation 3.16. Mandelic, 4-methylmandelic, and 4-methoxymandelic acids were produced in 75%, 80%, and 80% yields, respectively [24]. 

Camphorquinone, 77 Carbazole reaction, 9 Carbinol, o-aminophenyl methyl, 55 benzyl isopropyl, 54 phenyl ethyl, 54 phenyl methyl, 44, 54 phenyl ra-propyl, 54 Carone, 75 Carveol, dihydro-, 73 Carvone, 71, 72 Catechol, 39, 42 4-chloro-, 42... 

In addition to phenol and acetone, there are obtained minor amounts of other products such as acetophenone, a-methylstyrene and phenyl dimethyl carbinol. The yield of phenol on benzene is about 85%. The economics of the process are bound up with the value of the co-product, acetone and a decline in the use of acetone for the production of methyl methacrylate (see section 6.2.2) could have a major effect on the profitability of the cumene process. 

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... 

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]... 

Weiterhin wurden aus 2-Phenyl-2-o-tolyl-athanoI-[f-14C] (III) und l-Methyl-9-fluorenyl-(carbinol-[14C]) (V) durch Wagner-Meerwein-Uhi-lagerung das o-Methylstilben IV und das -Methylphenanthren (VI) dargestellt, um den sterischen Effekt der o-Methylgruppe auf den Verlauf der Umlagerung zu untersuchen (25). 

Allylic and benzylic alcohols were oxidized to aldehydes or ketones with BnPhsPHSOs in refluxing CHsCN. The yield increased in the presence of bismuth chloride in a catalytic amount. Selective oxidation of various alcohols under solvent free conditions was also reported Interestingly, benzyl alcohols were oxidized selectively to benzaldehydes in very high yield (95-100%) when reacted with BnPhsPHSOs (1.2 eq.) and AICI3 (1 eq.) in the presence of an equimolar amount of 2-phenethyl alcohol, diphenyl carbinol or methyl phenyl sulfide (equation 72). 

Trade Names. Phenoxanol (IFF), Phenylhexanol (Firmenich), Mefrosol (Quest). l-Phenyl-3-methyl-3-pentanol [10415-87-9], phenethyl methyl ethyl carbinol... 

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...

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