Methyl benzyl carbinol

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 ... 

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... 

Reaction of the dilithiated species 416 and 419 with alkyl halides, aliphatic and aromatic aldehydes, and TMSC1 leads to products 421 and 422 in modest yields (Scheme 129) [83TL4735 86JCR(S)20]. In cases of the N-benzyl amides corresponding to 415 and 418, small amounts of benzylic functionalization is observed (see also later). The methyl and carbinol derivatives corresponding to 421 and 422 were quantitively hydrolyzed into useful synthons 423 and 424, and 425 and 426, respectively. 

Methyl n-amyl carbinol. 247, 254 Methyl n-amyl ketone, 482 Methylaniline (mono), pure, from commercial methylaniline, 562, 570 P-Methylanthraquinone, 728, 740 Methyl benzoate, 780, 781 p-Methyl benzyl alcohol, 811,812 Methyl benzyl ketone, 727, 735 Methyl y-bromocrotonate, 926, 927 2-Methyl-2-butene, 239 Methyl n-butyl carbinol, 247,255 Methyl n-butyl ether, 314 Methyl n-butyl ketone, 475, 481 4-Methylcarbostyril, 855 p-Methylcinnamic acid, 719 4-Methylcoumarin, 853, 854 Methyl crotonate, 926, 927 Methylethylacetic acid, 354, 358 Methylethylethynyl carbinol, 468 Methyl ethyl ketone, 335, 336 purification of, 172 Methyl n-hexyl ether, 314 Methyl n-hexyl ketone, 335, 336 Methyl n-hexyl ketoxime, 348 Methyl hydrogen adipate, 938 Methyl hydrogen sebacate, 938,939 4-Methyl-7-hydroxycoumarin, 834 Methyl iodide, 287 Methyl isopropyl carbinol, 247,255 Methyl 4-keto-octanoate, 936... 

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. 

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. 

Benzyl Alcohol Diphenyl Oxide Methyl Isobutyl Carbinol Propylene Giycd ... 

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

Dimethyl p-tolyl carbinol. See Tri methyl benzyl alcohol... 

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

Phenylethyl methyl ethyl carbinol. See 1-Phenyl-3-methyl-3-pentanol Phenylethyl methyl ethyl carbinol acetate. See Phenethyl methyl ethyl carbinyl acetate P-Phenylethyl methyl ketone. See Benzyl acetone... 

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)... 

Synonyms Benzenemethanol, a,a,4-trimethyl- 8-p-Cymenol p-Cymen-8-ol Dimethyl p-tolyl carbinol 8-Hydroxy-p-cymene a-Hydroxy-p-cymene p-(Hydroxyisopropyl) toluene 1-Methyl-4-(a-hydroxyisopropyl) benzene 1 -Methyl-4-(1 -hydroxy-1 -methylethyl) benzene 2-(4-Methylphenyl)-2-propanol p-Tolyl dimethyl carbinol 2-(p-Tolyl)-2-propanol a,a,4-Tri methyl benzenemethanol a,a,4-Trimethylbenzyl alcohol p,a,a-Tri methyl benzyl alcohol Empirical C10H14O... 

Methyl-2.4.6-tii thyl-anisol 8 II514. n-Hexyl-bensyl-cwfainol ft II515. j9-[4-Oxy-phenylJ-oct ii ft, 564. Dipropyl-benzyl-carbinol ft 1273. II515. Dliso pyl.benzyl-ovrbinol ft 1273. /J-O -y-methyl-y-ithyb/J-phonyl-pentMi... 

A series of newly-discovered constituents, present in traces only, has also been described by H. Masson. These bodies are as follows methyl-amyl-carbinol, metbyl-heptyl-carbinol, benzyl alcohol, and di-methyl-furfurol. 

The search for opioid analgesics which show reduced addiction liability ha.s centered largely on benzomorphan and morphinan derivatives. Some research has, however, been devoted to derivatives of the structurally simpler meperidine series. The preparation of one such compound, picenadol (59), starts with the reaction of N-methyl-4-piperidone with the lithium derivative from m-methoxybromobenzene. Dehydration of the first formed carbinol 51 gives the intermediate 52. Deprotonation by means of butyl lithium gives an anion which can be depicted in the ambident form 53. In the event, treatment of the anion with propyl bromide gives the product 54 from reaction of the benzylic anion. Treatment of that product, which now contains an eneamine function. 

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°. 

Allylic and benzylic alcohols were oxidized to aldehydes or ketones with BnPhsPHSOs in refluxing CHsCN. The yield increased in the presence of bismuth chloride in a catalytic amount. Selective oxidation of various alcohols under solvent free conditions was also reported Interestingly, benzyl alcohols were oxidized selectively to benzaldehydes in very high yield (95-100%) when reacted with BnPhsPHSOs (1.2 eq.) and AICI3 (1 eq.) in the presence of an equimolar amount of 2-phenethyl alcohol, diphenyl carbinol or methyl phenyl sulfide (equation 72). 

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