Stannous chloride dihydrate → Allyl 3-allyloxy-4-aminobenzoate

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Reaction Steps

The crude ester (10 g, 38 mM) was dissolved in ethanol (20 ml) and added to a stirred suspension of SnCl2.2H2O (42.9 g, 0.19M) in ethanol (60 ml) under argon at ambient temperature. The mixture was heated to reflux for 30 minutes, cooled and poured onto ice. After making basic to pH 8 with an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4 and evaporated to give allyl 3-allyloxy-4-aminobenzoate (8.2 g).

Provenance & Evidence