1- Methyl-1-phenylethanol

Methyl-1 -phenylethanol Phenyidimethylcarbinol Phenyl isopropanol 2-Phenylisopropanol 2-Phenyl-2-propanol 2-Propanol, 2-phenyl-Empirical C9H12O... 

Methyl-1-phenylethanol. Seea-Cumyl alcohol Methyl phenyl ethanolamine. See2-(N-Methylanilino) ethanol... 

Numerous autoxidation products (e.g., 1,3- and 1,4-dihydroxybenzene, 1,3- and l,4-di-[l-methylethyl]benzene dihydroperoxide, 1-methyl-1-phenylethanol) were separated from their 1,3- and 1,4-diisopropylbenzene parent compounds on a silica column (2 = 257 nm) with a 98/2 hexane/IPA mobile phase [610]. Each set of compounds (i.e., the 1,3 vs. the 1,4) was studied separately. Lower limits of... 

Propylene oxide is a colorless, low hoiling (34.2°C) liquid. Table 1 lists general physical properties Table 2 provides equations for temperature variation on some thermodynamic functions. Vapor—liquid equilibrium data for binary mixtures of propylene oxide and other chemicals of commercial importance ate available. References for binary mixtures include 1,2-propanediol (14), water (7,8,15), 1,2-dichloropropane [78-87-5] (16), 2-propanol [67-63-0] (17), 2-methyl-2-pentene [625-27-4] (18), methyl formate [107-31-3] (19), acetaldehyde [75-07-0] (17), methanol [67-56-1] (20), ptopanal [123-38-6] (16), 1-phenylethanol [60-12-8] (21), and / /f-butanol [75-65-0] (22,23). 

The hydroperoxide process involves oxidation of propjiene (qv) to propylene oxide by an organic hydroperoxide. An alcohol is produced as a coproduct. Two different hydroperoxides are used commercially that result in / fZ-butanol or 1-phenylethanol as the coproduct. The / fZ-butanol (TBA) has been used as a gasoline additive, dehydrated to isobutjiene, and used as feedstock to produce methyl tert-huty ether (MTBE), a gasoline additive. The 1-phenyl ethanol is dehydrated to styrene. ARCO Chemical has plants producing the TBA coproduct in the United States, Erance, and the Netherlands. Texaco has a TBA coproduct plant in the United States. Styrene coproduct plants are operated by ARCO Chemical in the United States and Japan, Shell in the Netherlands, Repsol in Spain, and Yukong in South Korea. 

Some alcohols that have been converted into the corresponding fluorides by reactions with diethyldminosulfur trifluoride include 1-octanol, 2-methyl-2-butanol, isobutyl alcohol, cyclooctanol, ethylene glycol, crotyl alcohol, 2-phenylethanol, 2-bromoethanol, ethyl lactate, and ethyl a-hydrox3maphthaleneacetate. ... 

Treatment of perhydropyrido[2,l-c][l,4]oxazine-3,6-dione 232 with B2H6 yielded (—)-(2i )-[(2S)-hydroxymethyl)piperldin-1 -yl]-2-phenylethanol (233) (00T233). Reduction of ( )-(3i ,4i ,9aS)-4-methyl-3-phenylperhydropyr-ido[2,l-c][l,4]oxazin-3-ol (234) with NaBH4 yielded ring-opened product 235 (97JHC1813). 

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]... 

Later on the crucial role played by the solvent was enlightened in the protease-catalyzed resolution of racemic amines [26]. As shown in Table 1.3, the ratio of the initial rates of acylation of the (S)- and the (Ji)-enantiomers or racemic a-methyl-benzylamine (9) varied from nearly 1 in toluene to 7.7 in 3-methyl-3-pentanol. Similarly, the same authors found a significant solvent effect for the subtilisin-catalyzed transesterification of racemic 1-phenylethanol (10) using vinyl butyrate as acyl donor (Table 1.4 [27]). 

Lipases from C. antarctica and P. cepacia showed higher enantioselectivity in the two ionic liquids l-ethyl-3-methylimidazolium tetrafluoroborate and l-butyl-3-methylimidazolium hexafluoroborate than in THE and toluene, in the kinetic resolution of several secondary alcohols [49]. Similarly, with lipases from Pseudomonas species and Alcaligenes species, increased enantioselectivity was observed in the resolution of 1 -phenylethanol in several ionic liquids as compared to methyl tert-butyl ether [50]. Another study has demonstrated that lipase from Candida rugosa is at least 100% more selective in l-butyl-3-methylimidazolium hexafluoroborate and l-octyl-3-nonylimidazolium hexafluorophosphate than in n-hexane, in the resolution of racemic 2-chloro-propanoic acid [51]. 

Although this chapter is directed toward ophthalmic products, it is largely applicable to parenteral and even nonsterile products (solutions, emulsions, and suspensions). The choice of preservative is limited to only a few chemicals that have been found, over the years, to be safe and effective for this purpose. These are benzalkonium chloride, thimerosal, methyl- and propylparaben, phenylethanol, chlorhexidine,... 

The secondary benzylic alcohol l-phenylethan-l,2-diol requires 20 hours of treatment at room temperature to produce a 64% yield of 2-phenylethanol (Eq. 43).137 Under the same conditions, methyl mandelate fails to undergo reduction, presumably because of the greater carbocation-destabilizing effect of a neighboring carboalkoxy compared to a hydroxymethyl group (Eq. 43).137... 

Adults of some species also produce 4-oxo-( )-2-alkenals. Other types of simple compounds that have been found in the defensive secretions of true bugs include common terpenoids such as a- and (3-pinenes, limonene, linalool, and Z, -oc-farnesene, and simple aromatic compounds such as benzyl alcohol, ben-zaldehyde,p-hydroxybenzaldehyde, methyl p-hydroxybenzoate,phenylethanol, and guaicol. In general, although a number of species may share particular components, each species does appear to produce its own particular blend. In at least one species, the blend of defensive compounds is reported to vary with season and/or diet [36]. 

Enantiomers of 2,7-dimethyl-l,6-dioxaspiro[4.5]decane 28 Enantiomers of 2-Ethyl-7-methyl-l,6-dioxaspiro[4.5]decane 29 Enantiomers of 2,8-dimethyl-l,7-dioxaspiro[5.5]undecane 30 5 - Methylh eptan - 2 -ol (Z)-Non-3-en-l-ol 3,7-Dimethyloctan- l-ol Benzaldehyde 2-Phenylethanol Phenylacetonitrile Isobutyl benzoate Isopentyl benzoate Hexadecanoic acid 17-Hydroxyan drost-4-en-3-one (2)-Octadec-9-enoic acid... 

Racemization of chiral a-methyl benzyl cation/methanol adducts. The rate of exchange between water and the chiral labeled alcohols as a function of racemization has been extensively used as a criterion for discriminating the Sn2 from the SnI solvolytic mechanisms in solution. The expected ratio of exchange vs. racemization rate is 0.5 for the Sn2 mechanism and 1.0 for a pure SnI process. With chiral 0-enriched 1-phenylethanol in aqueous acids, this ratio is found to be equal to 0.84 0.05. This value has been interpreted in terms of the kinetic pattern of Scheme 22 involving the reversible dissociation of the oxonium ion (5 )-40 (XOH = H2 0) to the chiral intimate ion-dipole pair (5 )-41 k-i > In (5 )-41, the leaving H2 0 molecule does not equilibrate immediately with the solvent (i.e., H2 0), but remains closely associated with the ion. This means that A inv is of the same order of magnitude of In contrast, the rate constant ratio of... 

Scheme 6.3 Reaction scheme for the hydrogenation of acetophenone. AP acetophenone PE 1-phenylethanol CHMK cyclohexyl methyl ketone CHE 1-cyclohexylethanol ST styrene EB ethylbenzene and ECH ethylcyclohexane.

Table 6.13 Racemic hydrogenation of acetophenone" initial reaction rate rf, selectivity to products at 100% conversion. Results for the chemical reduction with NaBH4 are included for comparison. PE 1-phenylethanol, CHMK cyclohexyl methyl ketone and CHE 1-cyclohexylethanol. (Reproduced from Reference [34])...

Certain alkaloids are able to effect asymmetric induction during a reduction process at a mercury cathode even when present in low concentration in an aqueous alcohol acetate buffer. Asymmetric induction under these conditions was first observed [39] during the conversion of 4-methylcoumarin to 4-methyl-3,4-dihydro-coumariit (sec page 60). Induction results because a layer of alkaloid is strongly adsorbed on the electrode surface thus permitting transfer of a proton to a carban-ion intermediate m an asymmetric environment. Up to 16% asymmetric induction has been achieved in 1-phenylethanol recovered from reduction of acetophenone in a buffer of pH 4.8 containing a low concentration of quinidine. lire pinacol formed simultaneously shows no optical activity. However quinidine is itself reduced at the potential employed so that the actual catalyst for the asymmetric process is not defined [34,40],... 

Ephedrine Ephedrine, L-erythro-l-phenyl-2-methylaminopropanol-l (11.3.4), is synthesized from benzaldehyde in a few different ways. According to the first, benzaldehyde is condensed with nitroethane, giving 2-methyl-2-nitro-l-phenylethanol (11.3.2), which is reduced to 2-methyl-2-amino-l-phenylethanol (11.3.3). The necessary L-isomer is isolated from the mixture of isomers by crystallization. Methylation of this gives ephedrine (11.3.4) [52,53]. 

The first variant works with isobutane as the hydroperoxide precursor, which is oxidized to TBHP by molecular oxygen. During the epoxidation of propene, TBHP is transformed to ferf-butanol, which is converted to methyl ferf-butyl ether. The second procedure employs ethylbenzene, which is oxidized by molecular oxygen to phenyl ethyl hydroperoxide, which transfers an oxygen to propene and so is reduced to phenylethanol. This by-product of the process is converted to styrene, a versatile bulk chemical. 

Phenylacetate, methyl Sd (roasted)"" Phenylethanol, 4-methyl Sd Hu""° Phosphoric acid inorganic Sd"" ... 

Methyl thieno[3,2-r/][l,2,3]thiadiazole-6-carboxylate (MTTC) 50 has been shown to deactivate the P450 enzyme-catalyzed oxidation of 1-phenylethanol to acetophenone <1997B7209>. It was postulated that this was due to preferential enzymatic oxidization of MTTC. GC-MS analysis of the enzymatic oxidation products of compound 50 showed the major product to have a molecular mass of 188. Compounds 51 or 52 are possible structures assigned to this molecular mass although no other analytical method had been used for confirmation. 

Figure 20. Simultaneous enantiomer separation of various classes of compounds ( Schurig test mixture 184) on CP-Cyclodextrin-/3-2,3,6-M-19 (permethylatcd /3-cyclodextrin in OV-1701) [25 m x 0.25 mm (i.d.) column, 70°C for 5 min followed by 3cC/miu, 0.65 bar hydrogen]143. 1+2 2,6,6-trimethylbicy-clo[3.1.1]hept-2-ene (x-pinene), 3 ( + )-(lJR)-//ms-2,6,6-trimethylbicyclo[3.1. l]heptane (pinane), 4 (-)-(lS )-fra/M-pinanc. 5 (-)-(lS)-fw-pinane, 6 ( + )-(l/J)-cw-pinane, 7 + 8 2,3-butancdiol. 9 meso-2,3-butanediol, 10 + 11 tetrahydro-5-methyl-2-furanone (y-valerolactone). 12 + 13 1-phenylethanaminc. 14 + 15 1-phenylethanol, 16 + 17 2-ethylhexanoic acid.

Methyl cinnamate Cinnamaldehyde 2-Phenylethanol 1-Phenylethanol Phenylacetaldehyde... 

Alcohol dehydrogenase (Regeneration of co-factor is Reduction of acetophenone to (R)-phenylethanol in phosphate buffer/ methyl tert-butyl ether [27]... 

---