Methanol → (2,6-Dinitrophenyl)methanol

Participants

Reaction Steps

11.0 g of sodium borohydride were dissolved in 160 ml of 0.2N sodium hydroxide at room temperature. The resulting solution was dropwise added to a methanol solution comprising 100 g of 2,6-dinitrobenzaldehyde. This was stirred for 30 minutes at room temperature. Afterwards, methanol was removed therefrom by distillation, and the residue was extracted several times each with diethyl ether. The ether extracts were dried with anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure, using a rotary evaporator, and the residue was recrystallized three times each from chloroform/carbon tetrachloride, to obtain 90.2 g of 2,6-dinitrobenzyl alcohol. 20 g of this 2,6-dinitrobenzyl alcohol and 23.7 g of p-toluenesulfonyl chloride were dissolved in 150 ml of acetone to prepare a solution. An acetone solution comprising 2.25 ml of dicyclohexylamine was dropwise added to the solution and stirred at 25° C. for 24 hours. Afterwards, the reaction mixture was treated and recrystallized in the same manner as in the treatment of the above-mentioned 2,6-dinitrobenzyl alcohol, and 22.3 g of 2,6-dinitrobenzyltosylate (photo acid generator a) having the following formula were obtained. ##STR18##

Provenance & Evidence