Butyl picolinate

Chloro-5-trifluoromethylpyridine, an iatermediate to the herbicide flua2ilop—butyl, can be made from ( -picoline by two processes. ( -Picoline is chloriaated to 2-chloro-5-trichloromethylpyridine [69405-78-9], followed by fluoriaation with hydrogen fluoride under pressure (200°C, 10 h) (441) or vapor-phase (350°C, CCl diluent) conditions (442). An alternative process features the siagle-step vapor-phase reaction of ( -picoline with chiorine—hydrogen fluoride (400°C, N2 or CCl diluent) (443). 

The piedominant use of P-picoline (3) is as a starting material for agrochemicals and pharmaceuticals. For example, it is used to make insecticides such as chlorpyrifos (43), food additives such as niacin (27) and its amide (26), and herbicides such as fluazifop-butyl [69806-50-4] (63). 

The most thoroughly investigated compounds are the alkyl-pyridines. Coleman and Fuoss compared the reactions of pyridine, 4-picoline, and 4-isopropylpyridine with n-butyl bromide and found a steady increase in the rate in the order given the activation energies are 16.0,15.95, and 15.6 kcal per mole, respectively. Brown and Cahn carried out a detailed study of the reactions of 2-, 3-, and 4-alkyl-pyridines with methyl, ethyl, and isopropyl iodides in nitrobenzene the results are given in Table II. These data show the higher activation... 

Cyclazines are an interesting class of compounds that can be synthesized by intramolecular cyclization to the 3-position of the indolizine ring.200 The reactivity of the methyl group in 5-methylindolizine is similar to that in 2-picoline, and this provides the means of preparing cycl[3,2,2]azines. Thus, the reaction of 5-methyl-2-phenylindolizine with butyl lithium followed by JV,JV-dimethylbenzamide yielded the 5-(phenacyl) derivative, which could be ring-closed to 133 by heating... 

PICOLINIC ACID. 5-BUTYL-, CALCIUM SALT. HYDRATE... 

Tyrosine 4-Picoline Butyl lithium Palladium on charcoal... 

Oxidation of A-diethylphosphito to A-diethylphosphono derivatives 151 has been performed using 2-picoline A-oxide, MCPBA, diphenyl selenoxide, or 7-butyl hydroperoxide (TBHP). The latter was selected as the most efficient reagent. Similarly, the N-phosphitylated /3-sultams undergo reactions of oxidative addition of elemental sulfur and selenium giving 2-thio- and 2-selenophosphono /3-sultams 152 and 153, respectively, in satisfactory yields (Scheme 46) <1999HAC61>. 

More interestingly, in the same report the authors observed that the quantum yield for the TCA-sensitized photooxygenation of 25 substantially increased by carrying out the reactions in the presence of catalytic amounts of acid (tri-fluoroacetic acid 10 2 10 3 M) or nucleophiles such as pyridine, 2-t-butyl-pyridine, 4-picoline [99]. 

Diphenyl carbonate from dimethyl carbonate and phenol Dibutyl phthalate from butanol and phthalic acid Ethyl acetate from ethanol and butyl acetate Recovery of acetic acid and methanol from methyl acetate by-product of vinyl acetate production Nylon 6,6 prepolymer from adipic acid and hexamethylenediamine MTBE from isobutene and methanol TAME from pentenes and methanol Separation of close boiling 3- and 4-picoline by complexation with organic acids Separation of close-boiling meta and para xylenes by formation of tert-butyl meta-xyxlene Cumene from propylene and benzene General process for the alkylation of aromatics with olefins Production of specific higher and lower alkenes from butenes... 

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