Sodium borohydride → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

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Reaction Steps

Sodium borohydride (39.7 g) is added in portions to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzaldehyde (336 g) in methanol (3.36 liters), the reaction temperature being maintained at 0°-5° C. When the addition is complete, the batch is stirred for a further 60 minutes at room temperature and concentrated under reduced pressure, and the residue is partitioned between ice-cooled 2N hydrochloric acid and ethyl acetate (3×2 liters). The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution, added over magnesium sulfate and concentrated. Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4) yields the title compound in the form of an oil (326 g): Rf (ethyl acetate/hexane 2:1)=0.31. Anal. C12H18O4 (226.27): calc. C, 63.70; H, 8.02; found C, 63.70; H, 8.24.

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