Oxidation of anisyl alcohol

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. 

Table III. Oxidation of anisyl alcohol by TDCSPPFeCl in aqueous solution in the presence of veratryl alcohol (pH 3)...

Table IV. Oxidation of Anisyl Alcohol by TDCSPPFeCl and mCPBA in Aqueous Solution in the Presence of 1,4-dimethoxybenzene (pH 3)...

Teunissen, P.J.M. and J. A. Field. 1998. 2-Chloro-l,4-dimethoxybenzene as a novel catalytic cofactor for oxidation of anisyl alcohol by lignin peroxidase. Appl. Environ. Microbiol. 64 830-835. 

Hydroboration-oxidation of (E) 2 (p anisyl) 2 butene yielded an alcohol A mp 60°C in 72% yield When the same reaction was performed on the Z alkene an isomenc liquid alcohol B was obtained in 77% yield Suggest reasonable structures for A and B and describe the relation ship between them... 

Protection of primary alcohols p-Anisyl ethers are readily prepared from primary alcohols by the Mitsunobu reaction [P(C6H5)3 DEAD]. The ethers are stable to 3 N HC1 or 3 N NaOH at 100°, to Jones or PCC oxidation, and to LiAlH4. Deprotection is effected in 85-95% yield by oxidation with CAN in aqueous CH3CN. 

Alcohol A is a racemic mixture of the 2S,3R and 2R,3S enantiomers of 3-(p-anisyl)-2-butanol. Hydroboration-oxidation of the Z alkene gives alcohol B. 

Lund 12°) was first in applying cpe in the oxidation of a primary alcohol to an aldehyde (which under constant current conditions would be partly or completely oxidized to the corresponding carboxylic acid) 121 Anisyl alcohol displays two anodic waves in acetonitrile-sodium perchlorate withiTj /2 of 1.22 and 1.64 V vs. Ag/0.1 M Ag Cpe at the plateau of the first wave (1.35 V) in the same medium consumed only 5 % of the theoretically calculated amount of electricity and no carbonyl compound was formed. Addition of a three-fold excess of pyridine (to act as a proton acceptor) gave a 72 % of anisaldehyde ... 

This method was introduced by Polonski and Chimiak 192,193) in 1974 (Scheme 47). It is based on the oxidation of Schiff bases (239) to appropriate oxaziridines (240) in ether using monoperphtalic acid (MPP). Bases (239) are obtained from esters of amino acids and anisyl aldehyde (238) and are oxidised without isolation. Oxaziridines (240) are next hydrolyzed with hydrochloric acid to N-hydroxyamino acids (1) or give p-toluenesulfonates of (76, 213), which crystallize readily, by splitting with hydroxylamine j7-toluenesulfonates in alcohol. Use of benzaldehyde is unfavourable and leads to nitrones. Use of mono-perphthalic acid permits one to follow the progress of the reaction due to precipitation of phthalic acid. This method is general. Because bases (239) racemize only very slowly it is possible to obtain 193) optically active compounds (1,76, 213). 

This is isolated in the usual manner from di-p-anisyl telluride. It sinters at 180° C. and melts at 183° to 184° C. The crystals consist of four-sided columns, easily soluble in warm benzene, toluene, xylene or chloroform, less soluble in alcohols, carbon disulphide or carbon tetrachloride, insoluble in petroleum ether. Boiling with water for a prolonged period yields a product of which the tellurium content lies between that of the dichloride and that of the oxide. 

Benzyl alcohols [95] and ethers [96] may be oxidized anodically. This has been employed in an anodic removal of benzylic protecting groups. Anisyl ethers of the protected alcohols were preferred because of the relatively low oxidation potential of these ethers [1.65 V (SCE)] [97] ... 

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