2- Methyl-4-phenyl-2-butanol

Dimethyl-3-phenyl-1 -propanol 0,0-Dimethyl-5-phenylpropyl alcohol 2-Methyl-4-phenyl-2-butanol 2-Methyl-4-phenylbutan-2-ol Phenylethyl dimethyl carbinol 2-(2-Phenylethyl )-2-propanol 4-Phenyl-2-methyl-2-butanol 4-Phenyl-2-methyl-butanol-2 1-Propanol, 1,1-dimethyl-3-phenyl-Classification Aromatic alcohol Empirical CnHieO... 

Phenyl-2-methyl-2-butanol 4-Phenyl-2-methyl-butanol-2. See Dimethyl phenethyl carbinol... 

Phenyl-2-butanol has a methyl group, an ethyl group, and a phenyl group (—Cgl ) attached to the alcohol carbon atom. Thus, the possibilities arc addition of ethylmagnesium bromide to acetophenone, addition of methylmagnesium bromide to propiophenone, and addition of phenylmagnesimn bromide to 2-butanone. 

In performing a retrosynthetic analysis, it may also be useful to disconnect a bond, showing the fragments not as real compounds but only as an electrophile and a nucleophile. (The electrophile and nucleophile fragments are called synthons.) This may help bring to mind other reactions that can be used to reassemble the fragments. Thus, the disconnection of 3-methyl-1-phenyl-1-butanol can be written as shown in the following equation ... 

When a bond is disconnected, two polarities of the fragments are possible. Either fragment can potentially be the nucleophile, while the other is the electrophile. Let s consider the disconnection of the other carbon-carbon bond involving the hydroxybearing carbon of 3-methyl-1-phenyl-1-butanol. The disconnection shown in the following equation suggests another Grignard pathway ... 

The same system was employed in the reduction of 4-phenyl-2-butanone to (S)-4-phenyl-2-butanol using HLADH as well as 5-ADH from Rhodococcus sp. with high enantioselectivity [113]. With pentamethylcyclopentadienyl-4-ethoxy-methyl-2,2 -bipyridinechloro-rhodium(III) as mediator and HLADH as catalyst, after 5 h 70% of 4-phenyl-2-butanone was reduced to (S)-4-phenyl-2-butanol with 65% ee. Using 5-ADH. 76% of the ketone was converted to the (S)-alcohol after 5 h with 77% ee. Furthermore, this system has been applied in an electrochemical EMR with a polymer bound rhodium complex as mediator. 

The reagent tris[3-t-butylhydroxymethylene)-D-camphorato]Eu(III) was used initially to separate the resonances of R and S enantiomeric amines [53]. The fluorinated reagent tris[3-trifluoroacetyl-D-camphorato]Eu(III), Eu(facam)3 was used in the separation of resonances of enantiomers of 2-phenyl-2-butanol. The spectra of 2-phenyl-2-butanol on addition of Eu(thd)3 and Eu(facam)3 are shown in Fig. 10.21. As seen in the figure, Eu(thd)3 did not cause changes in the resonances while Eu(facam)3 caused separation of a-methyl resonances into two peaks, and resolved the -methyl triplets into a quintuplet and thus distinguishing the two isomers [54],... 

For closely related compounds, absolute configuration has been determined from NMR spectra in the presence of chiral shift reagents [55]. For compounds with greater structural differences there are many difficulties and uncertainties to overcome before concrete results can be obtained. One of the problems is the manner of variation of induced differential shift, AA5 of resonances of protons as a function of reagent-substrate molar ratio as shown for 2-phenyl-2-butanol in Fig. 10.23. It is clear from the figure that AA<5 for a-methyl resonances increase steadily, while for -methyl protons reaches a maximum, then declines and reaches plateau. For the ortho protons, a reversal in the sense of nonequivalence occurs at a molar ratio of approximately unity. Some of the implications of such a behaviour are both theoretical and practical. If the complex formation constants for enantiomers are different, then the sense of non-equivalence should be the same for all the proton resonances, and AA<5 should increase to a maximum and level off. Since this is not the case, different magnetic environments or stoichiometries of shift reagent-substrate adducts may be the factors for the observed anomalous variation of AA5. 

Genus, species Ethanol Ethyl acetate 3-Methyl- butyl acetate Ethyl octanoate 2-Methyl propanol 3-Methyl- butanol 2-Phenyl ethanol Acetic acid Acetaldehyde... 

Preparation and Stability. Since A -unsubstituted oxazo-lidines are labile to hydrolysis, they should be transformed immediately after preparation to amide derivatives, which show much higher stability. Thus reaction of (S)-3-amino-2-methyl-4-phenyl-2-butanol with acetone in the presence of a catalytic amount of p-Toluenesulfonic Acid produces (S)-4-benzyl-2,2,5,5-tetramethyloxazolidine. A -Acylation using acryloyl, cinnamoyl, and propanoyl chloride (Et3N, —78°C) gives the corresponding amides. The 7V-crotonoyl derivative is better obtained by the crotonoylation of (S)-3-amino-2-methyl-4-phenyl-2-butanol followed by acetalization with (Me)2C(OMe)2. 

Amino-2-methyl-4-phenyl-2-butanol is available from (S)-phenylalanine and MeMgl (4 equiv) diethyl ether, rt, 5 h, 58%. 

Cychdehydration. The sulfonic acid resin Ambcrlite-15 was found to be more satisfactory than Bradsher s reagent (2, 214), sulfuric acid, or formic acid for cyclo-dehydration of 2-methyl-4-phenyl-2-butanol (1) to 1,1-dimethylindane (2). ... 

Dimethylindane 665 85% Sulfuric acid (1.2 parts by volume) is added slowly to vigorously stirred 2-methyl-4-phenyl-2-butanol (1 part by volume) at 10°. Reaction appears to be instantaneous, but for certainty stirring is continued for another hour at room temperature. Then the mixture is diluted with water (10-15 parts by volume) and distilled. An oil separates in the distillate and is separated the aqueous distillate is returned to the distillation flask, and the mixture is redistilled. The oil is redistilled from aqueous alkali, separated from that distillate, dried over calcium chloride, and fractionated, giving 1,1-dimethylindane (65%), b.p. 191°. 

Methyl-4-phenyl-2-butanol acetate. See 2-Methyl-4-phenyl-2-butyl acetate... 

---