1-Phenyl-2-methyl-2-propanol

C10H14N2O2 (S)-2-amino-3-(benzylamino)propanoic acid 119830-32-9 562.20 49.891 2 20057 Cl OH140 1 -phenyl-2-methyl-2-propanol 100-86-7 488.15 42.747 1,2... 

C10H14O 1 -Phenyl-2-methyl-2-propanol 298.2 5.71 0.21922E+02 -0.84231E-01 0.99475E-04 298-423... 

Synonyms Benzyl dimethyl carbinol 0,0-Dimethyl phenethy I alcohol 1,1-Dimethyl-2-phenylethanol DMBC 1-Phenyl-2-methyl-2-propanol... 

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)... 

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. 

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)...

Polymer extracts are frequently examined using GC-MS. Pierre and van Bree [257] have identified nonylphenol from the antioxidant TNPP, a hindered bisphenol antioxidant, the plasticiser DOP, and two peroxide catalyst residues (cumol and 2-phenyl-2-propanol) from an ABS terpolymer extract. Tetramethylsuccino-dinitrile (TMSDN) has been determined quantitatively using specific-ion GC-MS in extracts of polymers prepared using azobisisobutyronitrile TMSDN is highly volatile. Peroxides (e.g. benzoyl or lauroylperoxide) produce acids as residues which may be detected by MS by methylation of the evaporated extract prior to GC-MS examination [258]. GC-MS techniques are... 

BINAL-H reagents 45 are not effective in the enantioselective reduction of dialkyl ketones.53 For example, reaction of benzyl methyl ketone with (S)-45 gives (S )-l-phenyl-2-propanol in only 13% ee (71% yield). Reaction of 2-octanone with (R)-45 produces (S )-2-octanol in 24% ee (67% yield).53 This drop of ee values in the reaction may be explained by the lower energy difference between the favored transition state 48 and unfavored transition state 49 caused by the lack of the above-mentioned n-n repulsion between the reductant and the substrate dialkyl ketone. 

Melhyl-l-propanol Isobutyl Alcohol) and 2-Phenyl-1-propanol Herling and Pines (SO) studied the dehydration of 2-methyl-l-propanol and 2-phenyl-1-propanol. The two alcohols were passed over alumina under nonacidic conditions at temperatures of 350° and 270°, respectively (Tables III and IV). The 2-methyl-l-propanol underwent, in part, skeletal isomerization forming butenes, whereby the ratio of cisjtrans 2-butene produced was four to six times greater than the equilibrium ratio. The extent of skeletal isomerization depended to some extent on the method of preparation of the alumina. 

The crude product (10 g) is diluted with 4 mL of a solvent mixture (ethyl acetate/cyclohexane = 9 1). This solution is poured onto a column (75-mm diameter) filled with 120 g of silica gel (Merck 230-400 mesh) for flash chromatography. Elution is performed under gravity and requires 200 mL of the above solvent system, followed by 200 mL of ethyl acetate. 2-Phenyl-2-propanol mixed with methyl p-tolyl sulfide is eluted in the first fraction ( 150 mL, monitored by TLC). The subsequent fractions are collected ( 300 mL)... 

N-Benzyl-N-mesitylenesulfonyl)amino-1 -phenyl-1 -propanol Benzenesulfonamide, N-(2-hydroxy-1-methyl-2-phenylethyl)-2,4,6-trimethyl-N-(phenylmethyl)- (14) [R-(R, S )]-(187324-63-6), [S-(R, S )]-, (187324-64-7)... 

Lithium aluminum hydride reduction furnishes racemic 2-alkyl-l-alkanols in good yields13. Thus, from alkylation of 1,3-diacylimidazolidinone 1 with benzyl bromide followed by reduction, a 73% yield of ra< -2-methyl-3-phenyl-l-propanol is obtained. When this sequence is carried out with (R,R)-1 as starting material, (S )-2-methyl-3-phenyl-l-propanol is obtained in 93% ee [a]D -10.2 (c = 1.1, C6H6) 13. 

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). 

In the course of the continuing study [9a,b] on the enantioselective addition of dialkylzincs to aldehydes by using chiral amino alcohols such as diphenyl(l-methyl-2-pyrrolidinyl)methanol (45) (DPMPM) [48] A. A -dibutylnorephedrine 46 (DBNE) [49], and 2-pyrrolidinyl-l-phenyl-1-propanol (47) [50] as chiral catalysts, Soai et al. reacted pyridine-3-carbaldehyde (48) with dialkylzincs using (lS,2/ )-DBNE 46, which gave the corresponding chiral pyridyl alkanols 49 with 74-86% ee (Scheme 9.24) [51]. The reaction with aldehyde 48 proceeded more rapidly (1 h) than that with benzaldehyde (16 h), which indicates that the product (zinc alkoxide of pyridyl alkanol) also catalyzes the reaction to produce itself. This observation led them to search for an asymmetric autocatalysis by using chiral pyridyl alkanol. 

The reverse reaction consisting of the PCL-catalyzed hydrolysis of the esters of three primary alcohols 2-methyl-3-phenyl-1-propanol 4, 2-phenoxy-l-propanol 5 and solketal 6 was studied by Kazlauskas et al.61 An enhancement of the enantioselectivity E was observed when changing the solvent from ethyl ether/phosphate buffer to 30% n-propanol in phosphate buffer and when changing the substrate from 1-acetate to 1-heptanoate. The same enhancement in E value was observed with 5 but there was no significant increase towards the alcohol 9. 

Methyl magnesium chloride (3.0 Molar solution in THF, 790 mmol) was added dropwise over 30 min to the CeCI3 slurry at 0°C. After stirring 2 hours, the mixture was cooled to -5°C and a toluene (600 mL) solution of the ethyl 2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxy-propyl)benzoate (152 mmol) was added dropwise over 1 hour. The reaction mixture was stirred another hour before the addition of 2 M HOAc (600 mL) and toluene (600 mL). The organic layer was washed with saturated aq. NaHC03 and with brine. Concentration in vacuo and purification of the residue by flash chromatography (30% EtOAc in toluene) gave 63.48 g (91%) of the 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol. 

To a solution of 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol in THF was dissolved in THF (1 mL) and DMF (1 mL) at -40°C was added diisopropylethylamine (2.2 mmol) and then methanesulfonyl chloride (2.2 mmol). The mixture was stirred 2 hours with slow warming to -30°C. The methyl l-(thiomethyl)cyclopropaneacetate (2.3 mmol) was added to the cloudy reaction mixture followed by dropwise addition of potassium tert-butoxide/THF solution (4.4 mmol). The reaction mixture was stirred at -30°C for 3.5 hours before quenching it with 25% aq NH40Ac. Extraction with EtOAc, washing the organic layer with brine and evaporation of the solvents left a residue that was purified by flash chromatography (5%-10% EtOAc in toluene) giving 658 mg (53%) of methyl l ((((R) (3 (2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)methyl)cyclopropaneacetate. 

A completely different course of reaction was established when one or both benzylic protons in the benzyl alcohol molecule were replaced with phenyl or methyl substituents diphenyl methanol gives bis(diphenylmethyl) ether, while 2-phenyl-2-propanol was transformed to 2,4-diphenyl-4-methyl-l-pentene)106 (Scheme 40). 

In 1981, Hirao and others reported that the chiral borane-amine complex 25a, derived from (S)-prolinol and 1 equivalent of BH3 THF, enantioselec-tively reduced propiophenone to afford (R )-l -phenyl-1 -propanol (26) in 44% ee9 (Scheme 4.3h). The chiral complex 25b was even better than 25a, affording the same secondary alcohol in 60% ee. Two years after the initial disclosure, Hirao et al. uncovered a new catalyst system that improved the previous experimental conditions dramatically10 (Scheme 4.3i). When the chiral aminoalcohol 27, prepared from (S)-valine methyl ester hydrochloride and phenylmagnesium bromide, was used along with 2 equivalents of BH3 THF, the enantioselectivity of the alcohol 26 jumped to 94% ee. In addition, the reaction time was shortened to 2 hours. 

Genus, species Ethanol Ethyl acetate 3-Methyl- butyl acetate Ethyl octanoate 2-Methyl propanol 3-Methyl- butanol 2-Phenyl ethanol Acetic acid Acetaldehyde... 

---