3-Phenyl-propanol

SYNS BENZENEPROPANOL, PROPANOATE (9CI) PHENYLPROPYL PROPIONATE P-PHENYLPROPYL PROPIONATE 3-PHENYLPROPYL PROPIONATE 1-PROPANOL, 3-PHENYL-, PROPIONATE... 

Among the earliest reports in this area was that of Lmdemann,iMB who claimed that three products could be produced under various conditions, namely, l chk>ro-3-phe oxy-2-propanol, phenyl glycidyl ether, and l,3-dipbenc xy-2-propaDo) (Eq. 602). The last could be H+Btf... 

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. 

Direct Borohydride Reduction of Alcohols to Alkanes with Phosphonium Anhydride Activation N-Proovlbenzene. To a solution of 5.56 g (20 mmol) of triphenylphosphine oxide in 30mL of dry methylene chloride at CfC was added dropwise a solution of 1.57 mL (10 mmol) of triflic anhydride in 30mL of dry methylene chloride. After 15 min when the precipitate appeared, a solution of 1.36g (10 mmol) of 3-phenyl-1-propanol in 10 mL of dry methylene chloride was added and the precipitate vanished in 5 min. An amount of 1.5g (40 mmol) of sodium borohydride was added as a solid all at once and the slurry was stirred at room temperature for... 

Fig. 3. Synthesis of fluoxetine (31). 3-ChIoro-I-phenyl-I-propanol reacts with sodium iodide to afford the corresponding iodo derivative, followed by reaction with methylamine, to form 3-(methyl amin o)-1-phenyl-1-propan 0I. To the alkoxide of this product, generated using sodium hydride, 4-fluorobenzotrifluoride is added to yield after work-up the free base of the racemic fluoxetine (31), thence transformed to the hydrochloride (51)...

Condensation of vinyl chloride with formaldehyde and HCl (Prins reaction) yields 3,3-dichloro-l-propanol [83682-72-8] and 2,3-dichloro-l-propanol [616-23-9]. The 1,1-addition of chloroform [67-66-3] as well as the addition of other polyhalogen compounds to vinyl chloride are cataly2ed by transition-metal complexes (58). In the presence of iron pentacarbonyl [13463-40-6] both bromoform [75-25-2] CHBr, and iodoform [75-47-8] CHl, add to vinyl chloride (59,60). Other useful products of vinyl chloride addition reactions include 2,2-di luoro-4-chloro-l,3-dioxolane [162970-83-4] (61), 2-chloro-l-propanol [78-89-7] (62), 2-chloropropionaldehyde [683-50-1] (63), 4-nitrophenyl-p,p-dichloroethyl ketone [31689-13-1] (64), and p,p-dichloroethyl phenyl sulfone [3123-10-2] (65). 

Hexafluoro-2-phenyl-2-propanol may be recovered from mother liquors, recovered solvent, and the KBr salt cake by extracting the mixture with aqueous base. Neutralization of the aqueous phase gives the alcohol (13-23 g.) which is purified by distillation. 

This dialkoxydiphenylsulfurane has been prepared by the reaction of diphenyl sulfide, 2,2,2-trifluoro-l-phenyl-l-(trifluoromethyl)ethyl hypochlorite, and potassium l,l,l,3,3,3-hexafluoro-2-phenyl-2-propanolate and by the reaction of diphenyl sulfide with 1 equivalent of chlorine and 2 equivalents of potassium 1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanolate in diethyl ether. ... 

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. 

Gabriel has demonstrated the instability of 5,6-dihydro-1,3-4/f-oxazines by reacting the hydrobromide of 2-phenyl-5,6-dihydro-l,3-4i -oxazine (55) with water. Ring opening occurs with the formation of 3-aminopropylbenzoate which is rearranged into 3-benzamido-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-... 

To a stirred and refluxed suspension of 17 parts of 1,2-dibromoethane, 7.8 parts of sodium hydrogen carbonate and 50 parts of 2-propanol is added a mixture of 3.4 parts of dl-2-thio-1-phenyl-lmidazolidine, 9 parts of a 20% potassium hydroxide solution in 40 parts of 2-propanol over a period of about 1 hour. After the addition is complete, the whole is stirred and refluxed for an additional 3 hours. The reaction mixture is evaporated. To the residue are added 18 parts of a 15% potassium hydroxide solution. The whole is extracted with toluene. The extract is dried and evaporated. The oily residue is dissolved in acetone and gaseous hy-... 

Common Name 3-(4-carboethoxy-4-phenylpiperidino)-1-phenyl-1-propanol hydrochloride Structural Formula ... 

Common Name dl-norephedrine hydrochloride 2-amino-1-phenyl-1-propanol hydrochloride... 

To a solution of 4 g of sodium in 200 ml of n-propanol is added 39 g of homovanillic acid-n-propyl ester (boiling point 160°C to 162°C/4 mm Hg) and the mixture is concentrated by evaporation under vacuum. After dissolving the residue in 200 ml of dimethylformamide and the addition of 0.5 gof sodium iodide, 26.2 g of chloracetic acid-N,N-diethylamide are added drop-wise with stirring at an internal temperature of 130°C, and the mixture is further heated at 130°C for three hours. From the cooled reaction mixture the precipitated salts are removed by filtering off with suction. After driving off the dimethylformamide under vacuum, the product is fractionated under vacuum, and 44.3 g of 3-methoxy-4-N,N-diethylcarbamido-methoxy phenyl acetic acid-n-propyl ester are obtained as a yellowish oil of boiling point 210°C to 212°C/0,7 mm Hg,... 

The resulting white solid is collected on a filter, air dried, redissolved in 2,500 parts water at 95°C and the resulting solution treated with decolorizing charcoal and clarified by filtration. The cooled filtrate is made alkaline with ammonia and the product, crude 3-(1-piperidyl)-Tcyclohexyl-1-phenyl-1-propanol is collected. The hydrochloride melts with decomposition in ten seconds in a bath held at 258.5°C. The alcohol melts at 114.3° to 115.0°C, according to U.S. Patent 2,716,121. 

Figure 11.2 A Walclen cycle interconverting ( + ) and (-) enan tiomers of 1-phenyl-2-propanol. Chirality centers are marked by asterisks, and the bonds broken in each reaction are indicated by red wavy lines.

---