3-phenyl benzyl alcohol

Chloro-a-methyl-a-phenyl benzyl alcohol is prepared by the grignardization of / -chloro-aeetophenone with phenyl magnesium bromide. This on etherification by treatment with N-(2-chloroethyl) dimethyl amine yields the chlorphenoxamine (base) which is then dissolved in an appropriate solvent and eonverted to the hydrochloride by a stream of hydrogen chloride to form the official compoimd. 

The catalyst is inactive for the hydrogenation of the (isolated) benzene nucleus and so may bo used for the hydrogenation of aromatic compounds containing aldehyde, keto, carbalkoxy or amide groups to the corresponding alcohols, amines, etc., e.g., ethyl benzoate to benzyl alcohol methyl p-toluate to p-methylbenzyl alcohol ethyl cinnamate to 3 phenyl 1-propanol. 

In detergent perfumes, the stabiUty of vanillin is not always certain. It depends on the association made with other raw materials, eg, with patchouli, frankincense, cloves, most of the animal notes, and such chemicals as amyl saUcylate, methyl ionones, heflotropin, gamma undecalactone, linalool, methyl anthrarulate, benzyl acetate, phenyl ethyl alcohol, cedar wood derivatives, oak mosses, coumarin, benzoin. Pern balsam, and cistus derivatives. In some cases, these mixtures can cause discoloration effects. 

FIGURE 4.24 Adsorption chromatography of small molecules with a TSK-GEL G2500PWxl column. Column TSK-GEL G2500PWxl, 6 /tm, 7.8 mm X 30 cm. Sample (I) phenylacetic acid. (2) 3-phenylpropionic acid, (3) 4-phenylbutyric acid, (4) benzylamine, (5) 2-phenylethylamine, (6) 3-phenylpropylamine, (7) benzyl alcohol, (8) 2-phenylethanol, and (9) 3-phenyl-1 -propanol. Elution 0.1 M NaCIO, in water. Flow rate 2.0 ml/min. Temperature 65 C. Detection UV at 215 nm. 

With some important exceptions, drugs in this class are conceptually related to the phenyl ethanol amines by the interposition of an oxymethylene group between the aromatic ring and the benzyl alcohol. 

The soft heavier odours of the cyclo substituted aliphatic alcohols such as benzyl and phenyl-ethyl alcohols. 

It appeared that the impure alcohol isolated from balsam of Peru was, in fact, identical with nerolidol. When allowed to stand for three to four weeks with phenyl-isocyanate both alcohols yielded a phenyl-urethane, melting at 37" to 38°. A mixture of the two bodies suffered no depression in melting-point. The alcohols have the formula 15 260-The alcohol from balsam of Peru is therefore mixed with a small quantity -of an alcohol of higher specific gravity, the nature of which is still undetermined. Traces of benzyl alcohol were found in it, but not in sufficient quantity to account for the differences observed. Oxidation experiments did not throw any light on the question. It may therefore be safely assumed that the peruviol of Thoms consisted in the main of nerolidol, but contaminated with a substance of the same boiling-point to such an extent that its combustion figures pointed to the formula CjjH. jO instead of... 

Phenyl-ethyl alcohol, CgH. CHj. CHjOH, is the next highest homologue of the benzyl alcohol series. It is found naturally in rose -and neroli oils but as it is very soluble in water, it practically disappears from the distilled otto of rose and is dissolved in the rose water. Hence otto of rose with its beautiful perfume does not truly represent the odour of the rose. By the use of various isolated and synthetic bodies an artificial otto can be prepared which more closely resembles the rose odour than does the natural otto itself. But it is doubtful whether any really good artificial otto of rose can be prepared without some natural otto as its basis. 

Phenyl-ethyl alcohol, or benzyl carbinol, has been known for many years, but its powerful rose odour has been entirely overlooked, its discovery having been made by an ordinary research chemist and not a perfumery expert. Its preparation was described in the Berichte (9, 373) in 1876, but the product there noted was evidently impure, as its boiling-point is recorded as 212°. Commercial specimens vary greatly in both their odour and their keeping properties, some samples deteriorating in odour very rapidly. It is, therefore, very important to -obtain it in a state of the highest purity. It has the following characters —... 

Phenyl-propyl alcohol, CgH. CHj. CH.2. CHj. OH, is the next highest homologue of phenyl-ethyl alcohol, and is also known as hydro-cinnamyl alcohol. Like the last described bodies it has been known for many years, its first preparation being described in the Aivnalen (188, 202). It occurs as a cinnamic acid ester in storax, and as an acetic ester in cassia oil. It is prepared synthetically by the reduction of cinnamyl alcohol with sodium amalgam and water, or by the reduction of cinnamic or benzyl acetic esters with sodium and absolute alcohol. It has the following characters —... 

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°. 

However, none of these compounds can be easily resolved except TM (16) Itself. Me prefer to resolve as early as possible, (page T 94), so It is better to carry out the Diels-Alder reaction with acrylic acid and resolve acid (19) before adding the phenyl group by a Grignard reaction. The benzylic alcohol group in (20) can be taken out by metal-anunonia reduction. Syrithesis ... 

The availability of Nafion on silica has not only lowered the cost of the resin but also has made it versatile (Sun et al., 1997 Harmer et al., 1998). A number of industrially important reactions have been attempted, with considerable success, with these catalysts. Consider the Fries rearrangement of phenyl acetate to p-acetyl phenol (/t-hydroxy acetophenone). This has been accomplished by Hoelderich and co-workers (Heidekum, 1998). In the ca.se of alkylation of benzene with benzyl alcohol, Amberlyst-15 and p-toluene sulphonic acid are ineffective and Nafion on silica works well at 80 °C. 

The use of the phenyl phosphate group as both a solid support attachment site and a crucial binding element represents what has been referred to as a pharmacophore-linking strategy [26]. We explored a variety of phenyl phosphate tether functionalities to provide resins varying in substitution pattern and in chemical flexibility (Scheme 1 and Table 4) [22]. All phenyl phosphate resins were synthesized in batch quantities of 20 g or more. Resin synthesis began with the addition of either /mnethoxy-benzyl alcohol or benzyl alcohol to commercially available bis(diisopro-pylamino)chlorophosphine, followed by addition of the diversity phenol [(Ri)-OFl, DIAT (diisopropylamino tetrazole)]. Displacement of the... 

Under these solvent-free conditions, the oxidation of primary alcohols (e. g. benzyl alcohol) and secondary alcohols (e.g. 1-phenyl-l-propanol) is rather sluggish and poor and is of little practical utility. Consequently, the process is applicable only to a-hydroxyketones as exemplified by various examples including a mixed benzylic/ali-phatic a-hydroxyketone, 2-hydroxypropiophenone that delivers the corresponding vicinal diketone [106,107]. 

A chiral bis(oxazolinyl)phenylrhodium complex was found to catalyze the asymmetric hydrosilylation of styrenes with hydro(alkoxy)silanes such as HSiMe(OEt)2 (Scheme 7).47 Although the regioselectivity in forming branched product 27 is modest, the enantiomeric purity of the branched product 27 is excellent for styrene and its derivatives substituted on the phenyl group. The hydrosilylation products were readily converted into the corresponding benzylic alcohols 29 (up to 95% ee) by the Tamao oxidation. 

The procedure given here is essentially that described previously by the submitters2 and is based on the early work of Knoevenagel.8 2-Phenylindazole has been prepared by reduction of N-(o-nitrobenzyl)aniline with tin and hydrochloric acid,4 by reduction of N-(o-nitrobenzyl) -N-nitrosoaniline with tin and hydrochloric acid,5 by dehydration of 2-(phenylazo)benzyl alcohol,6 by elimination of acetic acid from 2-(phenylazo)benzyl acetate,7 by dehydrogenation of 3,3a,4,5,6,7-hexahydro-2-phenyl-indazole with sulfur,8 and by thermal decomposition of o-azido-benzalaniline.9... 

Benzophenone, conversion to ethyl /S-hydroxy-0,0-diphenylpro-pionate, 44, 57 Benzophenone oxime, 44, 52 Benzopyrazole, 42, 69 3-Benzoylpropionic add, condensation with benzaldehyde to give a-benzylidene-y-phenyl-A y -bu-tenolide, 43, 3 N-Benzylacetamide, 42,18 n-Benzyiacrylamide, 42,16 Benzyl alcohol, reaction with acrylonitrile, 42,16... 

The acyclic version of Larock s heteroannulation was successfully applied to the synthesis of highly substituted pyridines [166]. The annulation of rert-butylimine 210 with phenyl propargyl alcohol produced pyridine 211 regioselectively in excellent yield. The regiochemistry obtained was governed by steric effects. Furthermore, the choice of imines was crucial to the success of the heteroannulations. terr-Butylimine was the substrate of choice, since all other imines including methyl, isopropyl, allyl and benzyl imines failed completely to produce the desired heterocyclic products. 

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