3-Benzyloxy-4-methoxybenzaldehyde → HCID 23258950, compound

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Reaction Steps

50 mmol of 3-benzyloxy-4-methoxybenzaldehyde and 55 mmol of trimethylsilyl cyanide are heated together with 0.567 mmol of anhydrous zinc iodide for 4 hours under nitrogen and exclusion of moisture to 90°. The mixture is then taken up in 15 ml. of absolute tetrahydrofuran, and this solution is added dropwise to a suspension of 60 mmol of lithium aluminum hydride in 35 ml. of tetrahydrofuran. After heating the mixture for one hour to 60°, it is worked up as described in Example 1. Recrystallization from ethyl acetate produces 2-amino-1-(3-benzyloxy-4-methoxyphenyl)-ethanol, m.p. 100°-102°, in a 30% yield.

Provenance & Evidence