Sodium Hydroxide → 4-Chloro-3-[(prop-2-en-1-yl)oxy]aniline

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Reaction Steps

A suspension of 1.0 g of 3A and 5.3 g of stannous chloride dihydrate in 10 mL of absolute ethanol was heated for 1 hour. The resulting mixture was poured into 100 g of ice, then sufficient 10% aqueous sodium hydroxide solution was added, with stirring, to bring the pH of the mixture to 10. The mixture was extracted with ethyl acetate, then with ether. The combined extracts were washed with water, then brine, then dried (Na2SO4) and stripped of the solvents, to give 3-(allyloxy)-4-chloroaniline (3B), as a brown oil.

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