1,3-Benzodioxole-5-carboxaldehyde, 4-methoxy- → 2-Methoxy-3,4-methylenedioxybenzylalcohol

Participants

Reaction Steps

The reaction was carried out in the same manner in Example 23 except for using 0.22 g of 5% platinum on carbon catalyst. The amount of hydrogen absorption was 111% of the theoretical amount. After the reaction was over, the catalyst was filtered out and 2N NaOH aqueous solution was added to the reaction mixture to make the filtrate alkaline (pH 11). The resulting mixture was then extracted with ethyl acetate. The liquid extract was analyzed by GC and LC to show 1.32 g of 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal (yield 84%), 0.13 g of 2-methoxy-3,4-methylenedioxybenzyl alcohol (yield 13%) and 4 mg of 2-methoxy-3,4-methylenedioxy toluene (yield 0.4%), and 0.6 mg of 2-methoxy-3,4-methylenedioxybenzaldehyde of the starting material (conversion rate:100%). The selectivity to the desired 2-methoxy-3,4-methylenedioxy-N-methylbenzylamino dimethylacetal was 87%.

Provenance & Evidence