Benzenes 1- Phenyl-2-propanol

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,... 

Nitrobenzene, 2,4-dinitro-toluene and other benzene derivatives along with phenol, phenyl propanol and thiourea Spherisorb ODS-2, 3 pm Acetonitrile-4 mM Tris, pH 9.2 (60 40) or gradient elution to 80 20 435 mm x 50 pm i.d. 158 mm effective length 78... 

SYNS 3-BENZENEPROPANOL FEMA No. 2885 HYDROCINNAAfYL ALCOHOL (3-HYDROXYPROP-YL)BENZENED 7-PHENYLPROPANOL 3-PHENYL-PROPANOL 3-PHENYL-l-PROPANOL(FCC) PHENYLPROPYL ALCOHOL y-PHENWEPROPYL ALCOHOL S-PHENYLPROPYT ALCOHOL... 

Figure 4.24. An example of the use of a ternary solvent system to control mobile pha.se selectivity in reversed-phase chromatography. A, methanol-water (50 50) B, tetrahydrofuran-water (32 68) and C, methanol-tetrahydrofuran-water (35 10 55). Identification 1 = benzyl alcohol 2 = phenol 3 = 3-phenyl-propanol 4 = 2,4-dimethylphenol 5 = benzene and 6 = diethylphthalate. (From ref. [583] Elsevier)...

Benzene, 1,r-(1,2-ethanediyl-bis(oxy))bis-2,4,6-tribromo. See Bis (tribromophenoxy) ethane Benzene, 1,1 -(1,2-ethanediyl) bis 2,3,4,5,6-pentabromo-. See Decabromodiphenylethane Benzeneethanimidoyl chloride, N,4-dihydroxy-o-OXO-. See 2-(p-Hydroxyphenyl) glyoxylohydroximoyl chloride Benzeneethanol. See Phenethyl alcohol Benzeneethanol, p-methyl-. See 2-Phenyl propanol-1... 

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. 

The reaction mixture is boiled for half an hour under reflux. Thereafter the ether Is removed by distillation, until the inside temperature reaches 65°-70°C. The resulting benzene solution Is added to 95 cc concentrated hydrochloric acid containing ice for further processing. Thereby, 3-piperidino-1-phenyl-1-[A5-bicyclo-(2,2,1)-heptenyl-2]-propanol-1 of the summary formula is obtained. The compound melts at 101°C and its chloro-... 

The Friedel-Crafts alkylation of aromatic compounds by oxetanes in the presence of aluminum chloride is mechanistically similar to the solvolyses above, since the first step is electrophilic attack on the ring oxygen by aluminum chloride, followed by a nucleophilic attack on an a-carbon atom by the aromatic compound present. The reaction of 2-methyloxetane and 2-phenyloxetane with benzene, toluene and mesitylene gave 3-aryl-3 -methyl-1-propanols and 3-aryl-3-phenyl-l-propanols as the main products and in good yields (equation 27). Minor amounts of 3-chloro-l-butanol and 4-chloro-2-butanol are formed as by-products from 2-methyloxetane, and of 3-phenyl-l-propanol from 2-phenyloxetane (73ACS3944). 

For example, in the optical resolution of diltiazem, a benzothiazepin derivative, with optically active mandelic acid, one of the diastereomeric salts with the same stereochemical sign (+) (+) or (-) (-) is crystallized from ethyl acetate whereas another with the opposite stereochemical sign (+) ( ) or (-) (+) is obtained from a mixed solvent of ethyl acetate and benzene (1 1).21 In the resolution of 1-phenyl-2-(p-tolyl)ethylamine with the same chiral acid, the same sign salt crystallizes from 50 % aqueous methanol and the opposite one from 2-propanol.22... 

To a solution of 0.4 mole of phenyl magnesium bromide in ether were added 42.3 g (0.183 mole) of hexamethyleneiminoethyl phenyl ketone, dissolved in dry ether, followed by 250 ml of dry benzene. The temperature of the mixture was slowly raised until all the ether had been driven off, after which the solution was heated to boiling under reflux of the benzene for 6 hours. The reaction mixture was then cooled and a solution of ammonium chloride was added. The benzene layer was washed with water and dried on potassium carbonate, filtered from the potassium carbonate, and the solvent was then evaporated. Recrystallization of the residue from petroleum ether (B.P. 60-80°C) yielded 44 g of l,l-diphenyl-3-hexamethyleneimino propanol-1 with a melting point of 81°C. 

Hydrogenation of cinnamaldehyde to 3-phenylpropionaldehyde over palladium catalyst may be accompanied by the formation of 3-phenyl-1-propanol and propyl-benzene,218 although the formation of 3-phenylpropionaldehyde usually predominates.219,220 The composition of the products are widely affected by the nature of palladium catalysts, solvents, supports, and additives.216,221 The hydrogenation over Pd-Al203 in ethanol or over Pd-kieselguhr in acetic acid gave 3-phenylpropionalde-hyde quantitatively at room temperature and atmospheric pressure. The addition of a 1 1 ratio of ferrous chloride to palladium also resulted in quantitative formation of 3-phenylpropionaldehyde in the hydrogenation over 5% Pd-C in methanol.221 This result was contrasted with those obtained with platinum oxide where iron additives led... 

C9H12S 2-ethyl-(1-thiaethyl)-benzene 20760-06-9 501.15 45.056 1,2 17308 C9H13NO 3-amino-3-phenyl-1-propanol 14593-04-5 459.35 39.993 2... 

A mixture consisting of 254 parts of 2-nitro-l-phenyl-1-propanol. 600 parts of methanol, 90 parts of acetic acid, and 7 parts of Raney nickel catalyst, was reduced with molecular hydrogen under conditions similar to those set forth in Example 1. At the conclusion of the reduction, the charge was removed from the hydrogenation apparatus, and filtered. The filtrate was then distilled at atmospheric pressure up to a temperature of 80° C. to remove the methanol present. The still residue was next extracted with a 100-part portion of a 50-50 mixture of benzene butanol, in order to remove non-basic impurities from the crude reduction product. After considerable agitation, the resulting mixture was allowed, to settle, and the upper benzene-butanol layer discarded. To the aqueous solution of the phenyl amino propanol acetate (salt) was added 60 parts of sodium hydroxide in the form of a 50 percent solution. This treatment resulted in the formation of two separate layers. The upper layer, containing principally free phenyl amino propanol, was separated and distilled under reduced pressure (60-70 mm.) up to a temperature of 100° C. At this point the pressure was further reduced (1-2 mm), and substantially pure phenyl amino propanol was collected at 125° C. 

Six gms. of nitro compound are dissolved in 50 mL. of 95% ethanol, and 20 gms. of zinc pellets (20 mesh) are added, together with a few drops of ferric chloride. Then while stirring and with the temperature maintained at 40° C., 35 mL. of 12 N. sulfuric acid are added, drop wise, during the course of 1 hour. Stirring is continued at 40° C. for six hours, then for an additional 18 hours at 20-25° C. The solution is then decanted from the zinc, made very alkaline, and extracted with ether. Concentration of the latter yielded crystals of 2-amino-2-methyl-l-phenyl-1-propanol having a melting point prior to purification of 80-89° C. Recrystallization from hot benzene raised the melting point to 99-99.5° C. 

The f-butylated naphthalene derivative (18 equation 49) is of interest as an intermediate for the synthesis of fungicides. Tetrahydronaphthalene derivatives, such as (20), have been evaluated as antifertility agents. Sugita et al. have studied the AlCb-catalyzed Friedel-Crafts alkylation of benzene with l-phenyl-2-propanol and 2-phenyl-1-propanol in the presence of additives, such as CuCb, CU2CI2 and decalin. Highly regioselective formation of 1,1-diphenylpropane was observed with Cu or Cu chloride as the additive. Some pertinent results of synthetic value are shown in Scheme 5. The addition of decalin diminished the alkylation reaction to give Ae reduction product 1-phenylpropane. 

Epoxides have occasionally been used in Friedel-Crafts reactions, and some interesting stereochemical observations have been made in this context. Quite unlike secondary alcohols which give almost fully racemized product, it has been shown that optically pure propylene oxide with AlCh and benzene gives optically pure 2-phenyl-1-propanol with inversion of configuration at the cleaved center. AlBrs leads to much lower levels of optical purity it was demonstrated that both starting material and product are optically stable to the reaction conditions, and therefore partial racemization is intrinsic to the mechanism with AlBrs. It is nonetheless clear from these and other results that even powerful Lewis acids do not assure reaction via simple planar carbenium ions. 

Catechin 1 -Cyclohexyl-4-(4-arylcyclohexyl)piperazines 1 -d-Ribofuranosylbenzimidazole 1 -Naphthylisothiocyanate 1 -Phenyl-2-decanoylamino-3-morpholino-1-propanol l,2-Diarylimidazole-4-carboxamides l,3,5-Triphenyl-2-pyrazolines l,4-bis-[2-(3,5-Dichloropyridyloxy)]benzene (TCPOBOP) ... 

S-ethyl, 2-(2 -imidazolyl)-4-ethenylphenyl (l-(N-tert butoxycarbonylamino)-2-phenyl) ethylphosphonate, S -0- (N-tert-butoxycarbonyl-L-phenylalanyl) -2-( N-metha-cryloylamino)-3-(5 -imidazolyl) propanol or their derivatives MAA EDMA CH2CI2, CHCI3 or benzene Using substrate analog or transition state analog enantioselective ester hydorolysis of N-tert- butoxycarbonyl phenylalanine p-nitrophenyl ester [173)... 

A complication in this study was the observation of mixed second- and third-order kinetics with water or aniline as the trap (in 1,2-dimethoxyethane, DME). Deuterium labelling showed that both the second- and third-order reactions proceeded by way of the sulfene. More recent observations show that the third-order term is more pronounced in benzene (being seen with 2-propanol as the sulfene trap), and becomes less marked as the solvent polarity increases to DME and methylene chloride43. The original kinetic study42 also presented a case for an ElcB-like E2 process for the reactions of phenyl methanesulfonyl chloride with tertiary amines, and provided evidence that the sulfene is not formed via the sulfonylammonium salt, RS02NR3, i.e. by nucleophilic catalysis. 

---