More Milas Articles

[lugh]

Here's the requested procedure and articles by Milas, JACS 58, 1302 (1936); 58, 2345 (1937); 59, 543 (1937); 61, 1844 (1939); 62, 1844 (1940) & 81, 3115 (1958):

Experimental
Preparation of the Reagent.-To 100 cc. of 30% hydrogen peroxide (Albone C) was added 400 cc. of pure tertiary butyl alcohol and the solution treated with small portions of anhydrous sodium sulfate whereby two layers separated out. The alcohol layer, which contained most of the hydrogen peroxide, was removed and dried with anhydrous sodium sulfate and finally with anhydrous calcium sulfate (Drierite). A solution of 6.32% hydrogen peroxide in tertiary butyl alcohol was obtained, giving a recovery of 93.8%. This solution can easily be concentrated by vacuum distillation of the alcohol at room temperature to any desired concentration without any loss of the peroxide provided an all-glass apparatus is employed. When hydrogen peroxide solutions of this sort were allowed to stand at room temperature for over six months only a small decrease in hydrogen peroxide concentration  was noticed.

[Saddam_Hussein]

He also patented his invention.

Patent US2402566

- NA Milas. Hydroxylation of unsaturated carboxylic acid compounds and the like. (1946)

[...]

Vanillin from isoeugenol - Five grams of isoeugenol was mixed with 45 cc of 6.3% solution of hydrogen peroxide in anhydrous tertiary amyl alcohol and 0.02 g of vanadium pentoxide. The catalyst went into solution, which heated up spontaneously. The reaction was completed in about twelve hours when the mixture had become more intensely red. An analysis for the presence of vanillin by precipitating the p-nitrophenylhydrazone gave a yield of 66% of vanillin.

Anisaldehyde from anethole - To 5 g of anethole were added 45 cc of 6.3% solution of hydrogen peroxide in anhydrous tertiary amyl alcohol and 0.02 g of vanadium pentoxide. The catalyst went slowly into solution, which heated up almost to the boiling point of the solvent. The reaction was over in about two hours when the mixture became deep red and the peroxide had completely disappeared. Considerable amounts of acetaldehyde vapor came off during the reaction. The solvent was then removed under reduced pressure and the residue dissolved in glacial acetic acid. Aliquot parts of this were analyzed for anisaldehyde. The yield of anisaldehyde amounted to 55%. In addition to anisaldehyde some anisic acid was isolated from the reaction, and a small amount of a deep red solid which is presumably an addition product of vanadium pentoxide with anisaldehyde.

[...]

[lugh]

Another article on hydroxylation:

Catalytic Hydrogen Peroxide Oxidation of
Aromatic Hydrocarbons
J. W. Cook and R. Schoental
J. Chem. Soc. 1950, 47