Propanol 3-chloro-2- -3-phenyl

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). 

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-... 

NELjAc, ammonium acetate Npg, a-neopentyl-glycine DNZ, 3,5-dinitrobenzyloxycarbonyl Z, ben-zyloxycarbonyl Bz, benzoyl Ac, acetyl TFAE, 2,2,2-trifluoro-l-(9-anthryl)-ethanol IPP, 1-phenyl-propanol 2PP, 2-phenylpropanol 3CPP, 3-chloro-l-phenylpropanol ACN, acetonitrile EA, ethyl acetate. 

Hydrolysis products that may form in soil and in microbial cultures include A-phenyl-3-chloro-carbamic acid, 3-chloroaniline, 2-amino-4-chlorophenol, monoisopropyl carbonate, 2-propanol, carbon dioxide, and condensation products (Rajagopal et al., 1984). The reported half-lives in soil at 15 and 29 °C were 65 and 30 d, respectively (Hartley and Kidd, 1987). 

If a diastereomeric mixture of (S,S)-2,5-dimethyl-3.4-hexanediol esters 2 and 3 reacts with methylmagnesium bromide, the result is kinetic resolution, as verified for R1 = Bn. The diastereomeric mixture was prepared from the racemic ethylene glycol a-chloro boronic ester via transesterification with chiral diol. The products isolated were (S,S)-2,5-dimethyl-3,4-hexanediol [(/ )-2-phcnyl-l-methylethyl]boronate, diastereomeric ratio >95 5 as indicated by the rotation of the (/ )- -phenyl-2-propanol derived by deboronation with hydrogen peroxide, and (S,S)-2,5-dimethyl-3.4-hexanediol methylboronate. Phenylacetaldehyde was identified by 1H NMR4. 

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). 

Propane, 2,2-dimethyl-l-phenyl-, 55, 112 Propane, 2-isocyano-2-methyl-, 55, 96 1.3-Propanedithiol, 56, 9 Propanesulfonyl cyanide, 57, 89 Propanoic acid, 2-chloro-, 56, 70 2-Propanol, 58, 133... 

More recently Bradley and co-workers288 demonstrated a fourth significant product in this reaction to be l,3-dichloro-2-propanol. formed by addition of hydrochloric acid to epiehlorohydrin. These authors then showed that under suitable conditions phenyl glycidyl ether can be mode to react wjth a chlorohydrin. There are formed in this manner a new epoxide and l-chloro-D-phenoxy-2-propanol, ah... 

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. 

Alkylated barbituric acids, 6-chloro-a-methylcarbazole-2-aceticacid, 1-phenylethanol, 1-phenyl-1-propanol, dimethyl, 3,4,5,6-pentafluoro-benzyl alcohol, l-(2-naphthyl)-ethanol, 1 -(p-biphenyl)-ethanol Chirasil-Dex coated column, 0.15 pm... 

A mixture consisting of 3-amino-3-phenyl-l-propanol (6.6 mmol), 4-chloro-2-fluorobenzonitrile (6.4 mmol) and 1.2 ml /V,/V-diisopropylcthylamine was heated 5 hours at 140°C then cooled. The material was purified by chromatography with... 

Among the earliest reports in this area was that of Lmdemann, who claimed that three products could be produced under various conditions, namely, l chloro-3 ph noxy-2-propanol, phenyl glycidyl ether, and l,3-dipbenoxy-2-jiiropano) (Eq. W2). The last could be... 

WM found in. 68% yieid from i-phenyl-S-chloro-l-propanol and in 70% yield from the acetate of the latter. ... 

Figure 16.13 Comparison of the experimental (symbols) overloaded elution band profiles of the racemic mixture of the R and S enantiomers of 3-chloro-l-phenyl-l-propanol on a Chiracel OB-H 250 x 4.6 mm column eluted with n-hexane/ethyl acetate, 95/5 v/v and the profiles calculated with the equilibrium-dispersive (dotted lines) and the transport-dispersive models (solid lines). Sample volume, 1 ml, loading factor Lj = 5%. Reproduced with permission from D. Cher-rak, S. Khattahi, G. Guiochon, J. Chromatogr. 877 (2000) 109, (Figure 7d).

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