1- Propanol, 3-chloro-, acetate

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. 

Propanol, titanium (4+) salt, 65, 230 2-Propanone, l-bromo-3-chloro-, dimethyl acetal, 65, 32 Propargyl bromide (106-96-7), 66, 77, 79, 86... 

The 3-chloro-l-(4-indolyloxy)-2-propanol is dissolved in 50 ml of toluene and 50 ml of isopropylamine and heated to the boil for 45 h. Evaporation to dryness is effected in a vacuum, the residue is shaken out thrice between ethyl acetate and a 1 N tartaric acid solution and a 5 N sodium hydroxide solution is then added to the combined tartaric acid phases until an alkaline reaction is obtained. The alkaline solution is shaken out thrice with 50 ml of methylene chloride, the extracts are dried over magnesium sulfate and the solvent evaporated in vacuum. The residue is crystallized from ethyl acetate/ether to give the 4-(2-hydroxy-3-isopropylaminopropoxy)indole. 

To 31 g of l,l-diphenyl-3-hexamethyleneimino propanol-1, dissolved in chloroform, an excess of thionyl chloride was added and the mixture was heated under reflux for 3 hours. Thereupon the reaction mixture was evaporated to dryness under reduced pressure and the residue was recrystallized by dissolving in warm ethanol and diluting this solution with ethyl acetate. An aqueous solution of the l,l-diphenyl-l-chloro-3-hexamethyleneimino propane hydrochloride thus obtained was hydrogenated with hydrogen gas in the presence of a buffered palladium-charcoal catalyst at a pressure of 3 atm. The l,l-diphenyl-3-hexamethyleneimino propane obtained was purified by distillation under reduced pressure. The boiling point was 170-174°C/1 mm. 

To a stirred solution of 28.4 parts of 1H-1,2,4-triazole in 135 parts of N,N-dimethylformamide were added 11.4 parts of a sodium hydride dispersion 80% under nitrogen atmosphere. After stirring for 1 hour at room temperature, a solution of 40 parts of 6-[chloro(4-chlorophenyl)-methyl]-l-methyl-lH-benzotriazole in 90 parts of N,N-dimethylformamide was added to the mixture. The whole was stirred for 1 hour at 60°C. The reaction mixture was diluted with 50 parts of water and the whole was evaporated. The residue was extracted with ethyl acetate. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (99 1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and l,l -oxy-bis-ethane (ether). The product was filtered off and dried, yielding 13 parts (29.2%) of 6-[(4-chlorophenyl)-(lH-l,2,4-triazol-l-yl)methyl]-l-methyl-lH-benzotriazole MP 178.9°C. A resolution of enantiomers any usual method gave crystals from 2-propanol, MP 130-135°C. [a]D20 = 8.0° (plus or minus) (c = 10 in CH3OH). 

C5H9Br 4-bromo-2-pentene 1809-26-3 391.15 36.310 1,2 5084 C5H9CI02 3-chloro-1-propanol acetate 628-09-1 437.15 37.880 1.2... 

C5H9Br 5-bromo-2-pentene 51952-42-2 388.08 35.320 2 5085 C5H9CI02 1 -chloro-2-propanol acetate 623-60-9 422.65 36.505 1,2... 

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

Amino-6-chloro-5-chloromethyl-3-cyanopyrazine with sodium acetate in dimethylformamide afforded 2-acetoxymethyl-5-amino-3-chIoro-6-cyanopyrazine (874), and 2-amino-5-chloromethyl-3-cyanopyrazine with potassium acetate in 2-propanol gave 5-acetoxymethyl-2-amino-3[Pg.165]

Bis-0-(2,4-dinitrophenyl) glycerin or 1,3 Bis(2,4 dinitrophenoxy)-2-propanol, (02N)2CgH3.0.CH2.CH(0H).CH2.0.C8H3(N02)2 mw 424.28, N 13.21% crysts (from acet), mp 173-5-174°(Pt block). It was obtd with other products by heating 4-chloro-1,3-dinitrobenzene with glycerin NaOH (Refs 2 6)... 

Transformation of 1,3-diamino-2-propanol (144) into vicinal diamines has been reported. Thus, the bis(benzyloxycarbonyl) derivative of (144) was mesylated to give (145), which was converted into 1-benzyloxycarbonylaziridine (146). Acetic acid and HCl reacted at the ring carbon of (146) affording 2,3-diamino-1-propanol (147) and l-chloro-2,3-diaminopropane (148 Scheme 68). On the other hand, the reaction of (146) with Grignard reagents and sodio malonates resulted in the loss of the carbamate protecting group. In contrast, the sulfonamide derivative (149) could be converted into diamines (151) and (152) via 1-tosylaziridine (150 Scheme 68). 

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).

Using indolyl-based substrate analogs such as 5-bromo-4-chloro-3-indolyl-ace-tate, butyrate, or propionate (X-acetate, X-butyrate, and X-propionate) for esterases and using the p-rosaniline assay coupled with ethanol, butanol, or propanol for alcohol dehydrogenases we were able to isolate several hundred candidates in the first level of a hierarchical screen. An intermediate screen was then used to characterize and compare the esterase candidates. We used nitrophenyl and methyl-umbelliferyl derivatives to analyze esterase candidates and their preference for chain length. 

The formation of acetals, by the acid catalyzed addition of hydroxyl compounds to a,/8-ethylene ethers is a useful method of protecting the hydroxyl group in reactions effected in basic media.—E 3-Chloro-l-propanol and dihydropyran, with a few drops of coned. HC1, allowed to stand for 3 hrs. with occasional shaking —> 2-(y-chloropropoxy)-tetrahydropyran. Y 78%. (F. e. s. W. E. Parham, E. L. Anderson, Am. Soc. 70, 4187 (1948).)... 

A solution of /7-chloroaniline in water (100 ml) and hydrochloric acid (80 ml) is diazotized at 0° by a solution of sodium nitrite (15 g) in water (30 ml). The clear (filtered, if necessary) diazonium solution is added to a cold solution of cinnamic acid (30 g) in acetone (250 ml). Then sodium acetate (44 g), followed by a solution of copper(n) chloride (8.5 g) in water (20 ml), are added. The temperature may rise slowly to 16° when gas evolution has begun. The mixture is stirred at 14-16° for 3 h. By the end of the coupling reaction two layers will have been formed — an upper layer of dark green oil and a lower layer of pale green aqueous acetone. The whole is distilled in steam. The residue is extracted in benzene and washed several times with 3N-ammonia solution and then with water. Distilling off the benzene leaves a crystalline residue of 4-chloro-stilbene which recrystallizes from 2-propanol in shiny leaflets, m.p. 129° (40%). 

Ethyl acetate extraction followed by GC with electron capture was used for routine, simultaneous determination of epichlorohydrin, 3-chloro-l,2-propanediol, and 1,3-dichloro-2-propanol in aqueous solutions of poly(amido amine)-epichlorohydrin resin. These impurities were detected at detection limits in the microgram per gram range [101]. 

Chloro-2-methylphenoxyacetic acid 2-(4-Chloro-2-methylphenoxy)propionic acid 2,4-Dichlorophenoxyacetic acid 2-(2,4-Dichlorophenoxy)propionic acid Ethers, Glycol Ethers l-Butoxy-2-propanol Butyldiglycol Butyldiglycol acetate Butyl glycol Butyl glycol acetate Butyltriglycol... 

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