Veratryl chloride

Swarts HJ, Mester T, Verhagen FJM, Field JA, Wijnberg JBPA (1997) The Formation of Veratryl Chloride by Bjerkandera sp. Strain BOS55. Phytochemistry 46 1011... 

A new procedure for the elaboration of benzylisoquinolines has been developed. Treatment of 6,7-dimethoxy-l-chloroisoquinoline with the Wittig reagent (16) prepared from veratryl chloride and tri-n-butylphosphine furnished, after workup, a 74% yield of papaverine. 

Also obtained by Friedel-Crafts reaction between veratryl chloride and phlrogluci-nol dimethyl ether, followed by demethy-lation of the obtained product [1505]. 

I. 4-methoxyacetophenone (30 //moles) was added as an internal standard. The reaction was stopped after 2 hours by partitioning the mixture between methylene chloride and saturated sodium bicarbonate solution. The aqueous layer was twice extracted with methylene chloride and the extracts combined. The products were analyzed by GC after acetylation with excess 1 1 acetic anhydride/pyridine for 24 hours at room temperature. The oxidations of anisyl alcohol, in the presence of veratryl alcohol or 1,4-dimethoxybenzene, were performed as indicated in Table III and IV in 6 ml of phosphate buffer (pH 3.0). Other conditions were the same as for the oxidation of veratryl alcohol described above. TDCSPPFeCl remaining after the reaction was estimated from its Soret band absorption before and after the reaction. For the decolorization of Poly B-411 (IV) by TDCSPPFeCl and mCPBA, 25 //moles of mCPBA were added to 25 ml 0.05% Poly B-411 containing 0.01 //moles TDCSPPFeCl, 25 //moles of manganese sulfate and 1.5 mmoles of lactic acid buffered at pH 4.5. The decolorization of Poly B-411 was followed by the decrease in absorption at 596 nm. For the electrochemical decolorization of Poly B-411 in the presence of veratryl alcohol, a two-compartment cell was used. A glassy carbon plate was used as the anode, a platinum plate as the auxiliary electrode, and a silver wire as the reference electrode. The potential was controlled at 0.900 V. Poly B-411 (50 ml, 0.005%) in pH 3 buffer was added to the anode compartment and pH 3 buffer was added to the cathode compartment to the same level. The decolorization of Poly B-411 was followed by the change in absorbance at 596 nm and the simultaneous oxidation of veratryl alcohol was followed at 310 nm. The same electrochemical apparatus was used for the decolorization of Poly B-411 adsorbed onto filter paper. Tetrabutylammonium perchlorate (TBAP) was used as supporting electrolyte when methylene chloride was the solvent. 

Poly B-411, a water-soluble, blue dye (IV) has been used as a lignin model by Glenn et al. (18). The dye was deposited onto a piece of filter paper, which was then attached directly to a glassy carbon anode. The anolyte contained 10 mM veratryl alcohol and 0.1 M tetrabutylammonium perchlorate (TBAP) in methylene chloride. The catholyte contained only... 

M TBAP in methylene chloride. After six hours controlled potential oxidation at 1.2 V, the blue color of filter paper on the side facing the anode turned to reddish brown. Complete oxidation of Poly B-411 in aqueous solution by TDCSPP FeCl and mCPBA gave the same color. The filter paper was not decolorized in a control experiment lacking veratryl alcohol. As Poly B-411 was not able to make direct contact with the electrode (since... 

The electrical potential and/or current required for electroenzymatic treatment have been shown to be lower than those needed in electrochemical treatment, which are not economically viable for large-scale. Electroenzymatic oxidation by peroxidases was proposed for the oxidation of veratryl alcohol by LiP [40], Then, electroenzymatic reactors have been used for the treatment of petrochemical wastewater [91], dyes, and textile wastewater [90, 92, 118] and phenol streams [93] utilizing peroxidase immobilized onto inorganic porous Celite beads or directly onto the electrode. The integration of a second electrochemical reactor, which generated hypochlorite in the presence of sodium chloride, has been used for indirect oxidation of the reaction products of the electroenzymatic treatment [91]. 

Synthesis. The first synthetic evidence for the structure of corydaline was provided by Koepfli and Perkin (255), who condensed /8-veratryl-ethylamine with 3,4-dimethoxy-a-methylhomophthalic anhydride to yield the amide LIX. The action of phosphoryl chloride on the methyl ester of LIX yielded the isoquinoline, probably LX, but formulated with... 

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