Sodium Hydroxide → 2-(7-Methoxy-2H-1,3-benzodioxol-5-yl)ethan-1-ol

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Reaction Steps

7.30 g (0.192 mol) of lithium alminium hydride was added to 270 ml of anhydrous tetrahydrofuran, and to this solution was added portionwise 33.68 g of 3-methoxy-4,5-methylenedioxyphenylacetic acid (2) with stirring under water-cooling. The mixture was stirred at room temperature for one hour, then added with 2.0 g (53 mmol) of lithium aluminium hydride and further stirred for one hour. The reaction mixture, while being cooled in an ice bath, was added portionwise with a solution of 9.3 ml of water and 10 ml of tetrahydrofuran and then further added portionwise with 9.3 ml of 15% sodium hydroxide aqueous solution. The resulting mixture was further added with 27.9 ml of water and then 500 ml of ethyl ether followed by stirring for 30 minutes. The deposited salt was filtered out and washed with ethyl ether. The filtrate and the ethyl ether used for washing were joined and concentrated under reduced pressure, and the residual oil was distilled in vacuo to obtain 19.09 g of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl alcohol (3) as an oil. Boiling point: 140°-142° C./ 1 mmHg: yield 68.4%.

Provenance & Evidence