Chloride → 1'-Hydroxyestragole

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Reaction Steps

Instead of the cinnamyl bromide, the chloride may also be used. Illustrative of its preparation is the following procedure: To the Grignard reagent, prepared from 2.25 g of magnesium, 9.75 g of vinyl bromide and 50 ml of tetrahydrofuran, the solution of 10.2 g of 4-methoxybenzaldehyde in 75 ml of diethyl ether is added dropwise while stirring under nitrogen and cooling with ice. The mixture is stirred for 2 hours at room temperature, again cooled, and 12 ml of saturated aqueous ammonium chloride are added dropwise. The resulting suspension is filtered, the filtrate dried and evaporated, to yield the 4-methoxy-α-vinylbenzyl alcohol.

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