Sodium hypochlorite Ascorbic acid

The Constitution of Ascorbic Acid. Action of Sodium Hypochlorite on a-Methoxy-acid Amides, R. G. Ault, W. N. Haworth, and E, L. Hirst,/. Chem. Soc., 1722 (1934). 

The primary hydroxyl group in 2,3 4,6-diisopropylidene-L-sorbose was oxidized with sodium hypochlorite in the presence of NiCls by Weijlard, who obtained a 90% yield of 2,3 4,6-diisopropylidene-2-keto-L-gulonic acid monohydrate. This reaction is normally carried out with permanganate for the production of ascorbic acid, but a wartime shortage of this oxidant caused the consideration of chlorine as a substitute. Similar results were found by Beer and Preobrazhenskii in more concentrated solutions. The yield of product was lowered drastically when the concentration of sodium hydroxide was less than 30%, when the chlorine-sorbose molar ratio was less than 4.1 and when... 

A yield of 60 to 70% of 3,5 4,6-di-0-ethylidene-L-gulonic acid can be readily obtained by the oxidation of one mole of 1,3 2,4-di-0-ethylidene-D-glucitol in the presence of one mole of alkali.According to a patent by D Addieco, this acid can be oxidized to 3,5 4,6-di-O-ethylidene-D-a 2/io-hexulosonic acid by sodium hypochlorite in the presence of nickelous chloride. After hydrolysis of the acetal groups, this acid can be rearranged to L-ascorbic acid. Thus, this provides, for vitamin C, a synthesis which does not require L-sorbose and does not involve bacterial oxidation. A 33% yield of D-xj/fo-hexulosonic acid is obtained. However, nothing is men-... 

L-ascorbic acid (ASC), sodium hypochlorite (NaOCl), hydrogen peroxide (H2O2), dimethyl sulfoxide (DMSO), acetone, acetaldehyde, and benzene were obtained from Fisher Scientific Company. 

The efficiency of the oxidation of 2,3 4,6-di-O-isopropylidene-a-L-sorbofuranose to 2,3 4,6-di-0-isopropylidene-a-L-arafciMo-hexulopyranosonic acid (a stage in the manufacture of L-ascorbic acid) with sodium hypochlorite and nickel sulphate (as a catalyst) has been shown to depend on the characteristics of the catalyst, the temperature of the reaction, and the concentration of the reactants. The catalytic activities of a number of metal cations e.g. Cu ", Ag", Co, Fe ", and Ce " ") in the electrochemical oxidation of 2,3 4,6-di-0-isopropylidene-a-L-sorbofuranose have also been examined, but none were as effective as Ni cations. ... 

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