Benzyl carbinol

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 —... 

The araliphatic alcohols mentioned above occur in many natural fragrances and flavors, but are generally not the main components. These alcohols are nearly always prepared synthetically for use in compositions. The branched-chain homo-logues of phenethyl and dihydrociimamic alcohols (dimethyl benzyl carbinol and dimethyl phenethyl carbinol, respectively) are used in fairly large amounts as fragrance materials, but have not been found in nature. 

Flowery Anisyl alcohol Benzyl acetate, phenylaceiate Cinnamic acid Cinnamyl acetate Citronellyl formate Crcsyl acetate Decanal Dimethyl benzyl carbinol Dimethyl benzyl carbinyl acetate Ethyl anthranilate Geranyl acetate Hydroxycitronellal dimethyl acetate Linalool Linalyl acetate Methyl benzoate Pcnethyl acetate 2-Phcnylpropionaldehyde 3-Phenylpropionaldehvde. 

It was hoped that the resulting benzylic carbinols 59 could be stereose-lectively reduced by catalytic hydrogenation to the required protected kainoid derivatives 60 (Scheme 24). The reduction of benzylic alcohols varies in stereospecificity depending on the catalyst employed.53 Hydrogenation over Raney nickel generally proceeds via retention of configuration, whereas hydrogenation over palladium on charcoal leads to inversion at the benzylic carbon. 

Dimethyl benzyl carbinol Menthol Linalyl acetate Eugenol... 

Dimethylamino-2-styrylethyl-quinolinium Iodide, 861 Dimethyl Anthranilate, 480, (Sl)70 Dimethyl Benzyl Carbinol, 480, 617 Dimethyl Benzyl Carbinyl Acetate, 480, 654... 

NJ I-DIMETHYLBENZYL aNE see DQP800 N> -DIMETHYLBENZYLAAnNE HEXAFLUOROARSENATE see BEL550 DIMETHYL BENZYL CARBINOL see DQQ200... 

Benzeneethanol benzyl carbinol benzylmethanol p-hydroxy-ethyl benzene PEA phenethanol p-phenylethyl alcohol 2-phenylethyl alcohol phenylethanol. 

By fractionated distillation receipt one 54 g dimethyl-benzyl-carbinol (36 % yield) and 80 g dimethylbenzylcarbinyl-formate (45% yield related to olefin). Source Bernhagen 1982... 

Evidence for the presence of organic cations was provided by bright red or purple colors observed immediately upon addition of the carbonyl compounds to the catalyst-aromatic mixtures, and by isolation of side products derived from hydride shifts to intermediate carbonium ions. Mechanistically, these reactions are visualized as proceeding by initial Bideal-like attack of aromatic on the adsorbed conjugate acid derived from the carbonyl compound, with the formation of an intermediate tert-benzylic carbinol ... 

Similarly, no ferf-benzylic carbinols were detected, with the single exception of the product from the reaction of phenol and hexafluoro-aoetone A) the failure of (A) to condense with another... 

An acceptable method is to oxidize methyl benzyl carbinol (l-phenyl-2-propanol) to phenylacetone (methyl benzyl ketone) with chrome oxide (CrO3) in pyridine solvent. The problem with this is that methyl benzyl carbinol is not commercially available, and so must be made from benzyl chloride grignard reagent and acetaldehyde. This grignard works well, although there can be a problem getting unreacted benzyl chloride out of the product. Their boiling points are very close, so distillation does not separate them completely. But the real question is Why make the synthesis of phenylacetone a two-step process when it can be done with one reaction ... 

B.49) (B.49) Benzeneethanol, phenylethylalcohol, 2-phenylethan-l-ol, /7-phenylethanol, benzyl carbinol [60-12-8] FEMA 2858... 

A variety of other intramolecular alkylation reactions have been utilized in the synthesis of indole alkaloids. The acid-catalyzed conversion of the alkene (78) to the cyclic product (79) is a key step in the synthesis of a brevianamide (Equation (19)) <9378471 >. Similar acid treatment of the benzylic carbinol (80) yields the )S-carboline derivative (81) (Scheme 20) <88CC623>. 

Synthesis of diaryl heteroarotinoids (11) and (12) [27,30,31] began with a Lewis acid-catalyzed cyclization of tertiary alcohol (34) to give dihydroben-zothiophene (36) as the sole isolated product. The chemistry of the ensuing steps was similar to that used to prepare (9) and (10) and other diaryl heteroarotinoids and involved (a) Friedel-Crafts acylation of a fused aromatic-heterocyclic system, (b) reduction of the resulting ketone to a benzylic carbinol, (c) phosponium salt formation, and finally (d), Wittig coupling to methyl 4-formylbenzoate. The free acids (13) and (14) were obtained by saponification. 

Synonyms cas 6O-12-8 phenylethyl alcohol 2-phenylethanol benzyl carbinol... 

Benzyl n-butyrate. See Benzyl butyrate Benzyl caprylate. See Benzyl octanoate Benzyl carbinol. See Phenethyl alcohol Benzylcarbinol isobutyrate. See Phenethyl isobutyrate... 

Benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone 2-Benzyl-2,N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone. See 2-Benzyl-2-(dimethylamino)-4 -morpholinobutyrophenone Benzyl dimethyl carbinol. See Dimethyl benzyl carbinol... 

Definition Obtained by esterification of dimethyl benzyl carbinol with n-butyric acid Empirical C14H20O2... 

Definition Synthesized from dimethyl benzyl carbinol and formic acid using acetic anhydride Empirical C11H14O2... 

Dimethyl-2-phenylethanol. See Dimethyl benzyl carbinol l-(Dimethylphenyl) ethan-1-one. See Dimethylphenyl methyl ketone Dimethyl phenylethyl carbinol. See Dimethyl phenethyl carbinol... 

DMB. See p-Dimethoxybenzene DMBA. See N-Benzyidimethylamine DMBC. See Dimethyl benzyl carbinol DMBCA. See Dimethyl benzyl carbinyl acetate DMBC butyrate. See a,a-Dimethylphenethyl... 

Isobutyl benzyl carbinol. Seea-Isobutylphenethyl alcohol Isobutylbis (hydroxymethyl) phosphine oxide CAS 142747-77-1... 

Synonyms Benzyl isoamyl alcohol Benzyl isobutyl carbinol Isobutyl benzyl carbinol 4-Methyl-1-phenyl-2-pentanol 4-Methyl-1-phenylpentan-2-ol... 

Synonyms Benzeneethanol Benzyl carbinol Ethanol, 2-phenyl- p-Hydroxyethylbenzene Methanol, benzyl-... 

Phenyl-2-methyl-2-propanol. See Dimethyl benzyl carbinol 3-Phenyl-2-methyl-propen-2-ol-1. See Methylcinnamyl alcohol 1 -Phenyl-3-methyl-5-pyrazolone CAS 89-25-8 EINECS/ELINCS 201-891-0 Synonyms Cl developer 1 Developer Z 2.4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one 3-Methyl-1 -phenyl-2-pyrazolin-5-one 3-Methyl-1 -phenyl-5-pyrazolone Norantipyrine Norphenazone 1-Phenyl-3-methyl-5-oxo-2-pyrazoline 1-Phenyl-3-methylpyrazolone-5 5-Pyrazolin-5-one, 3-methyl-1-phenyl-5-Pyrazolone, 3-methyl-1-phenyl-Empirical C10H10N2O Formula C6HsNN C(CH3)CH2CO Properties Wh. to It. yel. powd. orcryst. sol. 10-50 mg/ml in DMSO, 95% ethanol, acetone si. sol. in benzene sol. < 1 mg/ml in water insol. in ether, petrol, ether m.w. 174.20 vapor pressure < 0.01 mm Hg (20 C) m.p. 127-130 C b.p. 287 C (105 mm) ref. index 1.637 (20 C)... 

Dimethyl benzaldehyde Di methyl benzyl carbinol Dimethyl benzyl carbinyl acetate a,a-Dimethylbenzyl isobutyrate 2,6-Dimethyl-5-heptenal 2,6-Dimethyl octanal 3,7-Dimethyl-1-octanol a,a-Dimethylphenethyl butyrate a,a-Di methyl phenethyl formate... 

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