2-Methoxy-1 -phenylethanol

However, in the palladium-catalyzed addition of HSiCl3 to -substituted styrenes, the size of the substituent on the MOP ligand is crucial. While (R)-MeO-MOP/[Pd(//3-C3H5)Cl]2 yielded (R)-phenylethanol with poor enantioselectivity (14% ee),110 replacement of the methoxy group with hydrogen (H-MOP, (36d)) affords the same product with 93% ee (Equation (ll)) 111... 

Asymmetric esterification. me.vo-Cyclohexanedicarboxylic anhydride (1) undergoes a highly stereoselective esterification with the diphenylboric ester (2) of (R)-2-methoxy-l-phenylethanol in the presence of diphenylboryl triflate to provide,... 

Figure 15. Plots81 of the lanthanide-induced shift (LIS) for the methoxy group hydrogens in the two diastereomeric Mosher esters of 1-phenylethanol versus the molar ratio of Eu(fod)3.

The reinvestigation of this reaction has shown that styrene epoxide is formed as the initial product, but it rapidly undergoes isomerization to phenylacetaldehyde. In the presence of solvent methanol, however, addition of the solvent to the epoxide produces 32.8% of 2-methoxy-2-phenylethanol, decreasing the phenylacetaldehyde yield. In all cases the reaction is accompanied by further oxidation to benzaldehyde (Kumar et al., 1995). 

The products were separated by vpc or tic for their identification and quantitatively determined by vpc. For example, DPE gave benzo-phenone and its epoxide, which was converted to 2-methoxy-2,2-di-phenylethanol in methanol solution. 

Primary alcohols have been successfully used as substrates for lipases. Monterde et. Al60 reported the resolution of the chiral auxiliary 2-methoxy-2-phenylethanol 1 via Candida antarctica lipase B (CAL-B)-catalyzed acylation using either vinyl acetate (R=H) or isopropenyl acetate (R= CH3) as acyl donor (cf. fig. 8) and the alkoxycarbonylation using diallyl carbonate as the alkoxycarbonylation agent in THF at 30 °C (cf. fig. 9). 

Figure 8 Lipase-catalyzed enantioselective acylation of 2-methoxy-2-phenylethanol (rac-1) using either vinyl acetate or isopropenyl acetate as acyl donor.

Scheme 8.5 Metabolism of metoprolol, 28, is thought to involve "...rapid cleavage of the methoxyethyl chain at the methoxy group to afford a 2-phenylethanol derivative" [92] which is subsequently oxidized to the corresponding phenylacetic acid derivative, 28a [97]. Another metabolite is produced by oxidation of the...

Thirdly, in the case of completely or partially racemic alcohols, it is possible to create diastereomeric esters by reaction with one enantiomer of a chiral carboxylic acid. One acid that gives consistently good results is Mosher s acid, 3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid (52) (see Dale et al.u). With a chiral alcohol, e.g. 1-phenylethanol, a pair of diastereoisomers, 53 and 54, is formed (Scheme 8.5). 

Photolysis of (2-phenoxyphenyl)phenyldiazomethane (36) in cyclohexane at 10°C gave phenylcycloheptabenzofuran (37) via (2-phenoxyphenyl)phenylcarbene.The infrared spectrum of photo-chemically generated anthranylidene has been determined,and the dicarbene, (9,lO-dihydro-9,lO-o-benzeno-2,6-anthrylene)di(phenyl-methylene), has been shown by e.s.r. spectroscopy to have a quintet ground state.Products of photodecomposition 1,l-dimethyl-2-diazo-2-phenylethanol (38) in cyclohexane are the hydroxy ketone (39), the oxirane (40) and 3-phenylbutan-2-one (41), whereas reaction in methanol gave the methoxy alcohol (42) and the alkene (43).43... 

The ability to differentiate between two enantiotopic carbonyl groups in a symmetrical dicarboxylic anhydride in order to generate a chiral product is extremely useful, since the resulting product can be subsequently converted into either enantomeric species by selective transformations of the chemically distinguishable functional groups. (i )-2-Methoxy-l-phenylethanol (98), prepared from 63 by a four-step sequence, reacts in the presence of a... 

The KR of cyclic dicarboxyhc anhydride 15 was achieved by the reaction of 0.5 equiv of the diphenylboric ester of (R)-2-methoxy-l-phenylethanol 16. The diester 17 was produced with 90% de [43]. 

Preparation by oxidation of l-(4-hydroxy-3-methoxy-phenyl)-2-phenylethanol with DDQ in dioxane at r.t. for 16h(89%) [5177],... 

A mixture of 2-methoxy-2-phenylethanol, excess 2,2-dimethoxypropane, and dry Dowex-50-H ion exchange resin stirred and refluxed 3 hrs. 2-(2-melhoxy-2-phenylethoxy)-2-methoxypropane. Y 83.3% based on 2-methoxy-2-phenyl-ethanol consumed. F. e. s. G. E. Ham, J. Ghem. Eng. Data 8, 280 (1963). 

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