Hexanoic 6- -2-chloro

Acetic acid, butyryl-, ethyl ester [Hexanoic acid, 3-oxo-, ethyl ester] 55, 73, 75 Acetic acid, chloro-, tert-butyl ester [Acetic acid, chloro- 1,1-dimethylethyl ester], 55,94... 

Chlorosulfonic acid Sulfuric acid, chloro- (8,9) (7790-94-5) e-Benzoylaminocaproic acid Hexanoic acid, 6-benzamido- (8) Hexanoic acid, 6-benzoylamino- (9) (956-09-2)... 

TABLE 3. Synthesis of bicyclo [ .1.0]alkanes (82) from 1-chloro-vinyl p-tolyl sulfoxides (80) with lithium enolate of tert-butyl acetate, propionate and hexanoate through the adduct (81)... 

XAD-2 macroreticular resin columns. This situation implied that the XAD-2 column was not effective in retaining completely all the solutes present in the water samples. [NOTE The XAD-2 resin column contained about 25% more packing, and the rate of percolation was about the same as that normally used for processing 200 L of tap water (21).] In addition, a variety of volatiles that appeared immediately following the solvent peak were also present. Subsequent analysis of these concentrates by GC-MS indicated the presence of 6-chloro-2,4-diamino-1,3,5-triazine (tentative), 2,5-diphenylisoxazole (tentative), tributoxyethyl phosphate (confirmed), bis(2-ethylhexyl) phthalate (confirmed), and dimethylbenzoic acid (confirmed) from site 1. The concentrate from site 2, however, showed the presence of 2,4,5-trichlorophenol (confirmed), BHC (confirmed), 2,5-diphenylisoxazole (tentative), bis(2-ethyl-hexyl) phthalate (confirmed), trimethylbenzene (confirmed), ethylbenz-aldehyde (confirmed), ethylacetophenone (confirmed), hexanoic acid (confirmed), and 4-cyano-3,7,ll-tridecatriene (tentative). 

Heptanoate Methyl 5-Chloro-6,6-difluoto- ElOb,. 373 (F.duct) Hexanoate Ethyl 4-Chloro-5.5-diHuoro- E10b2, 373 (Educt)... 

Whereas several anti-cholestemic drugs are produced wholly by fermentation, the side chain of several others is accessible through enzymatic synthesis. (3R,5S)-Dihydroxyhexanoate, a key intermediate of fluvastatin, is accessible by reduction of the diketo acid, either by bioreduction with whole cells (85% yield, 97% e.e.), or cell extracts (72% yield, 98.5% e.e.), or, for syn-(3h,5.S)-dihydroxy-6-Cl-hexanoate, regioselective and (ft)-specific reduction with ADH to yield (5S)-6-chloro-3-ketohexanoate. 

Another way to statin side chains, via the intermediate syn-(i K,5,S )-6-chloro-hexanoate, employs regioselective and (K)-specific reduction with alcohol dehydrogenase (ADH) from Lactobacillus brevis to yield the intermediate (5S)-6-chloro-3-ketohexanoate from the 3,5-diketo acid (Wolberg, 2001) (Figure 13.16). Further reduction of (5S)-6-chloro-3-ketohexanoate to syn-(3R,5S)-6-chlorohexanoate is afforded chemically with NaBH4/B(OMe)Et2. 

An interesting effect was found whilst studying the enantioselectivity of these reactions. Although several esters (ethyl-2-chloropropionate, ethyl lactate, ethyl-2-hydroxy hexanoate and ethyl-2-methyl butyrate) were converted into the amides with only low to moderate ee values, the ammoniolysis of ibuprofen (2 -chloro-ethyl)ester was highly enantioselective. At 56 % conversion the ee of the remaining (S)-ester was 96% (Scheme 12.2-3), corresponding with an E value of the ammoniolysis of 28. 

The longest chain has six carbons, and the carboxyl carbon is automatically assigned the number 1. The parent compound is therefore hexanoic acid. The substituents are listed numerically to give the correct name of the compound 3-chloro-4,5-dimethylhexanoic acid. 

In an undivided cell the yields are reduced substantially. Methyl hexanoate gave (co — 1) and also some (co — 2) products. The selectivity of the reaction is reminiscent of the ester chlorination with N-chloro amines . In the anodic oxidation, however, carbocations seem to be involved, being formed most remote from the ester function. In suitable cases carbocation rearrangements are observed. 

Sodium EDTMPA. See Pentasodium ethylene diamine tetramethylene phosphonate Sodium 2-EHT. See Sodium 2-ethyl hexanoate Sodium endothall. See Endothall sodium Sodium epichlorohydrinsulfonate. See Sodium 3-chloro-2-hydroxy-1-propane sulfonate Sodium erythorbate... 

Pyrocine refluxed 4.5 hrs. with SOGlg in benzene, cooled, ethanol satd. with HGl added, and allowed to stand 15 hrs. at room temp. ethyl 5-methyl-5-chloro-3-(2-chloro-2-propyl)hexanoate. Y 91%. Also from isopyrocine s. M. Julia, S. Julia, and M. Langlois, Bl. 1965, 1014. 

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