Sodium Hydroxide → 4-(2,2-Dichlorocyclopropyl)phenol

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Reaction Steps

(-)-4-(2,2-Dichlorocyclopropyl)aniline (5 g, 0.024 mol) from the above resolution was dissolved in concentrated sulphuric acid (25 ml) and added in aliquots (1 ml) to iced water (100 ml). The mixture was allowed to stand overnight and the resulting precipitate then removed by filtration. The solid was suspended with stirring in sulphuric acid (0.05M, 70 ml) whilst being cooled to below 5° C. and a solution of sodium nitrite (2.2 g, 0.032 mol) in sulphuric acid (0.05M, 30 ml) added. After stirring for 1.5 hours the remaining precipitate was dissolved by addition of concentrated sulphuric acid (2.4 ml) and stirring maintained for a further 1.5 hours. The pH of the solution was then adjusted to 2 by addition of an aqueous solution of sodium hydroxide (10M) before being added to a stirred mixture of cupric nitrate hemipentahydrate (50 g, 0.21 mol) and sodium ascorbate (2.3 g, 0.012 mol) in distilled water (440 ml) and diethyl ether (150 ml). The mixture was stirred for 10 minutes before the organic phase was removed and the aqueous phase extracted with diethyl ether (3×100 ml). The combined organic phases were washed with distilled water, dried over anhydrous magnesium sulphate and the solvent removed by evaporation under reduced pressure to afford the crude (-)-4-(2,2-dichlorocyclopropyl)phenol (4.6 g) which was used directly in the following reaction.

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