Isopropyl benzyl alcohol

Isopropyl benzyl alcohol) (monoterpene) Commiphora myrrha (myrrh) (Burseraceae) [magi gift to infant Jesus], Glycyrrhiza glabra (Fabaceae) odour, burning taste)... 

Synonyms Cumic alcohol Cumin alcohol Cuminol Cuminyl alcohol Cumyl alcohol p-Cymen-7-ol 4-lsopropylbenzyl alcohol p-Isopropyl benzyl alcohol... 

C10H14O 4-isopropyl-benzyl alcohol 536-60-7 RI Temp/C Lambda/nm Ref. 

The alternative synthetic route using the sodium salt of benzyl alcohol and an isopropyl halide would be much less effective because of increased competition from elimination as the alkyl halide becomes more sterically hindered... 

The acetates of most alcohols are also commercially available and have diverse uses. Because of their high solvent power, ethyl, isopropyl, butyl, isobutyl, amyl, and isoamyl acetates are used in ceUulose nitrate and other lacquer-type coatings (see Cellulose, esters). Butyl and hexyl acetates are exceUent solvents for polyurethane coating systems (see Coatings Urethane polymers). Ethyl, isobutyl, amyl, and isoamyl acetates are frequentiy used as components in flavoring (see Flavors and spices), and isopropyl, benzyl, octyl, geranyl, linalyl, and methyl acetates are important additives in perfumes (qv). 

Isopropyl alcohol (IPA) or benzyl alcohol (toluol) often are used in the formulation (as early components in the order of addition) to dissolve the surfactant-detergent base [e.g., Duomeen OL (Akzo Nobel Chemicals, Inc.) or Triton N101 (Union Carbide Corp.)]. 

Butyl alcohol and benzene gave both mono- and di-i-butylbenzene (Simons et al., 37). Allyl alcohol reacted with benzene to produce both allylbenzene and 1,2-diphenylpropane. (Simons and Archer, 38.) The activity of the hydroxyl group is indicated in the fact that 2-phenyl-propanol was not separated. Benzyl alcohol reacted with benzene to form diphenylmethane (Simons and Archer, 39) despite the fact that this reaction is reported (Calcott et al., 34) to form 1,2,3,4,5,6-hexa-phenylcyclohexane by the polymerization of the alcohol. Isopropyl alcohol with benzene gave isopropylbenzene, 1,4-diisopropylbenzene,... 

In the Meerwein-Fonndorf reduction, cinnamaldehyde is reduced to cinnamic alcohol (yield ca. 85%) with isopropyl or benzyl alcohol in the presence of the corresponding aluminum alcoholate. 

Naftifine hydrochloride Naftin Cetyl alcohol, cetyl esters wax, isopropyl myristate, polysorbate 60, sorbitan monostearate, and stearyl alcohol Benzyl alcohol... 

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... 

The reactions of 4/3- acetoxythaliporphine (48) with nucleophiles have been studied. On dissolution in methanol, the 4-methoxy-analogue (49) is obtained, but the bulkier alcohols ethanol and benzyl alcohol require the presence of boron trifluoride etherate to generate the ethers (50) and (51). Loss of stereospecificity at C-4 was observed when isopropyl alcohol and cyclohexanol were the nucleophiles.33... 

The benzene is removed at atmospheric pressure, and the residue is distilled under reduced pressure from a 50-cc. Claisen flask. The fraction boiling at 89-91°/7 mm. consists of colorless benzyl alcohol weight 19 g. (89%). A small amount of higher-boiling material, benzyl benzoate, remains in the flask (with a 200% excess of aluminum isopropoxide in 200 cc. of isopropyl alcohol, the yield dropped to 65% and a larger high-boiling fraction resulted). 

Benzyl alcohol c7h8o Di-isopropyl ether (DIPE) CgHi40... 

Fig. 6.2. Electrochromatographic separation of benzyl alcohol (1), resorcinol (2), methylparaben (3), and p-naphthol (4) using a soft gel column (Reprinted with permission from [27], Copyright 1998 Wiley-VCH). Conditions Column 48.5 cm (24 cm active) x 75 pm i.d., stationary phase 4.1% T, 9.7% C, 0.7% S poly(2-acrylamido-2-methyl-l-propanesulfonic acid-co-N-isopropyl acrylamide-co-methylene bisacrylamide) mobile phase 20 80 acetonitrile and 2.5 mol/L phosphate buffer pH 6.8 16 kV.

Flow rate 3.0 ml/min. Solutes A = resorcinol B = theophylline C = phenol D = benzyl alcohol E = caffeine F = methyl paraben G = benzonitrile H = nitrobenzene I = cortisone J = propyl paraben K = ramrod L = butyl paraben M = chioro-isopropyl-N-(3-chlorophenyl) carbamate (CIPC) N = progesterone. Figure taken from ref. [627]. Reprinted with permission. 

DIHYDROXY-a-((ISOPROPYL-AMINO)-METHYL)BENZYL ALCOHOL... 

On the other hand, microbial treatment of simple alkyl-substituted aromatic compounds (e.g., 1-isopropyl-4-methylbenzene328 332) results in oxygenation of the methyl group, rather than the chemically more susceptible isopropyl group333. Further oxidation of the benzylic alcohol to the corresponding carboxylic acid is common and, in most cases, represents the only isolated product. 

L yanogen chloride reacts with isopropyl chloride in the presence of ferric chloride to give the hygroscopic complex (I) in high yield. The complex reacts with ethanol or sodium salt of benzyl alcohol to form the carbamates (3) and (4), respectively. 

The following alkoxypyrazines have been prepared from the corresponding dichloropyrazines and alkoxide ions 2,3-dimethoxy-5,6-dimethyl(and diphenyl) (797) 2,3-dibenzyloxy (sodium benzyl oxide in benzyl alcohol at reflux for 24 hours (883)] [but 23-dichloropyrazine with sodium hydride and benzyl alcohol in xylene gave l,4-dibenzyl-2,3-dioxo-l,2,3,4-tetrahydropyrazine)(988)] 2-chloro-5-methoxy (838) 2,5-diethoxy-3,6-dimethyl (872) 2methanolic sodium methoxide refluxed for 2 h) 2,5-dimethoxy-3-phenyl (817) 2-chloro-5-methoxy(and ethoxy)-3,6-diphenyl (817) 2,5-dimethoxy-3,6-dimethyl (and diisopropyl) (844) 2,5-dimethoxy-3-isopropyl-6-methyl (methanolic potassium methoxide at reflux for 6 days) (844) 2(5)-s-butyl-3-chloro-6-ethoxy-5(2)-isobutyl (93) 2-chloro-6-methoxy (838, 883) 2,6-dimethoxy (reflux for 8h) (832) 2,6-diethoxy (reflux for 14 h) (883) 2-benzyloxy-6-chloro (1 equiv. of sodium hydride and benzyl alcohol in benzene at reflux) (832) 2,6-dibenzyloxy (5 equiv. of sodium benzyloxide in benzene at reflux gave 70%) (832) and 3,5-dimethoxy-2-methyl (535). 

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