Sodium benzoate reduction

Although the reaction with thiosulfate and with iodide ions may be a mere reduction of the halide, the reaction with sodium benzoate would appear to be a radical dissociation induced by the attack of a negative ion. The fate of the benzoate ion is unknown. Tris-( -nitrophenyl)-methyl benzoate is a stable substance which does not dissociate into radicals.23... 

Nitration of hydroxypropiophenone (7-1) followed by conversion of the phenol to its methyl ether by means of methyl iodide provides the intermediate (7-2) the nitro group is then reduced to the corresponding amine (7-3) by catalytic reduction. The newly introduced amine is then replaced by a nitrile group by successive conversion to the diazonium salt by means of nitrous acid followed by treatment with cuprous cyanide (7-4). Reaction with aluminum chloride removes the methyl ether to afford the ortho acylphenol (7-5). This is converted to the chromone (7-6) as above by reaction with benzoyl chloride and sodium benzoate. The nitrile is next hydrolyzed to the carboxylic acid (7-7) by means of sulfuric acid. The acid is then converted to its acid chloride by means of thionyl chloride and that treated with 2-(A -piperidyl)ethanol (7-8). There is thus obtained flavoxate (7-9) [8], a muscle relaxant whose name reflects its flavone nucleus. 

Methylation of the lactam nitrogen and condensation with methyl benzoate in the presence of lithium diethylamide in THF afforded a ketone, which, on sodium borohydride reduction, yielded racemic isocynometrine (99) as the major component of a mixture of two epimeric phenyl carbinols (Scheme 8) (155). Racemic anantine (94) and cynometrine (95) have been synthesized analogously, starting from 4-formyl- 1-methylimidazole (155). 

The usual experimental procedure for carrying out reductions in the absence of an added proton donor entails the addition of a metal (Li, Na, K) to a solution of the substrate ketone in a mixture of NH3 and an ethereal cosolvent, usually ether or THF at the reflux temperature of liquid NH3. The metal is added until a permanent blue color is obtained and the reaction is stirred for 10 to 30 min. The excess Li is decomposed, traditionally with NH4CI or an alcohol however, sodium benzoate is probably superior. ... 

Comes, J.E. and Beelman, R.B. 2002. Addition of fumaric acid and sodium benzoate as an alternative method to achieve a 5-log reduction of Escherichia coli 0157 H7 populations in apple cider. Journal of Food Protection 65 476-483. 

Delphisine (43) was oxidized with Cornforth s reagent (Cr03-Py-H20) to yield 1-ketodelphisine (53) in 93% yield. Compound 53 was hydrolyzed with 5% methanolic potassium hydroxide solution at room temperature to give 1-ketoneoline (54) in 76% yield. The latter compound was converted into the corresponding benzoate (64) by treatment with benzoyl chloride and pyridine for 3 hr. Compound 64 was converted to 8-acetyl-14-benzoyl-l-ketoneoline (65) by treatment with acetic anhydride and catalytic amounts of p-toluenesulfonic acid on a steam bath for 1 hr. Sodium borohydride reduction of compound 65 yielded the desired product, 8-acetyl-14-benzoylneoline (63), and its C-l epimer (66). The structures of these compounds were confirmed by their H and 13C NMR analysis. 

Reduction of dichlorocarbene adducts. Reduction of the trans-cis mixture of the dichlorocarbene adducts (2) of 2-alkoxy-3,4-dihydro-2H-pyranes (1) gives 3-alkoxy-2-oxanorcaranes (3) in yields of 62-78% if sodium benzoate is used as... 

Irrational fears might result in irrational precaution. The US Food and Drag Administration published data on benzoic acid and ascorbic acid in 2007. Although no connection was established between the amount of these substances and the concentration of benzene, recommendations for the reduction in benzoate use were made for manufacturers in a few cases, which were duly followed. The British supermarket chain Sainsbury s removed sodium benzoate from 120 products because of consumer concerns. 

Ring cgntractions have been recorded in reductions and displacements of sulphonate esters. Treatment of the 6-deoxy-ditosylate (57) with lithium triethylborohydride gave the furanose (58), as well as the 3-reduced pyranoses (59) and (60), which arose via the mechanisms in Scheme 7. Substantial amounts of the DL-digino-furanoside (61) and the DL-rhodinofuranoside (62) were obtained by reaction of sodium benzoate in DiMF with the 4.-0-fflesylates of DL-... 

Carbohydrates are important chiral, non-racemic precursors (chiral templates) to statine and its derivatives. Aldehyde 6.138 0 as converted to alcohol 6.139 by reaction with isobutylmagnesium bromide. After conversion to a benzoate (6.140), displacement with sodium azide gave 6.141. The tetrahydrofuran ring was opened and oxidation gave 6.142. Oxidation of the aldehyde and then reduction of the azide moiety led to (+)-statine (3R,4S-tf.P5). Reaction of 6.139 with mesyl chloride and then sodium benzoate gave the benzoate (6.140) of opposite absolute configuration, which was converted to (-)-statine (3S,4R-t. 95) by the same sequence. 

Use of Equation 11.27 to estimate values of Ki gave the following results sodium acetate 92 litre moP S sodium benzoate 707 litre moP and sodium p-toluene sulphonate 950 litre moP The results of the study suggest that a negatively charged compound capable of hydrophobic interactions is required to prevent effective interaction of the CTAB micelles with the substrate. With amphipathic compounds such as the p-toluene sulphonates there is the possibility of the type of interactions that were discussed by Tomlinson et al [23]. Independent measurement of binding or interaction constants thus would be required before this mechanism of inhibition was elucidated. Charge reduction at the surface is likely to inhibit the access of OH ions to the substrate incorporated into mixed micelles . 

To synthesize alcohol with the reversed configuration at C-2, we started with the reduction of levoglucosenone to form the well-known alcohol (4) (Scheme 11.8). It was reacted with mesyl chloride to produce mesylate (28). The nucleophilic substitution was performed in refluxing toluene (or xylene) using sodium benzoate as a nucleophile and a nonnucleophilic phase transfer catalyst (tetrabutylammonium hydrogen sulfate) to give a very good yield of the expected benzoate (29). The hydrolysis of the... 

Benzyl alcohol and sodium benzoate are formed in the presence of sodium hydroxide. This change has often been referred to as an oxidation-reduction reaction, but experimental evidence has shown that oxidizing agents have no catalytic effect. This result would support the conclusion that the reaction is of the generalized acid-base type. 

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