Sodium Chloride → 4,4'-Dinitrobibenzyl-2,2'-disulfonate

Participants

Reaction Conditions

Reaction Steps

4,4'-Dinitrobibenzyl-2,2'-disulfonate was prepared as described in A. Ya. Zheltov, E. N. Avramenko, and B. I. Stepanov, Zhurnel Organicheskoi Khimii, 16, (2) 384-390 (1980), the disclosure of which is totally incorporated herein by reference. More specifically, 4,4'-dinitrobibenzyl-2,2'-disulfonate was prepared as follows. A solution (220 mL) of NaOCl (17.8 g) was prepared by passing chlorine through sodium hydroxide (20 g) in water (100 mL) with crushed ice (120 g) at 1° to 3° C. until the weight of the solution increased by 17 grams. To a stirred solution of 4-nitrotoluene-2-sulfonic acid (90.4 g, obtained from Pfaltz & Bauer, Waterbury, Conn.) in water (1 L) at 60° C. was added sodium hydroxide (16.8 g), NaOCl solution (50 mL), and gradually a solution of sodium hydroxide (200 g) in water (470 mL). To the resulting suspension was added NaOCl solution (120 mL). The reaction mixture was stirred 25 minutes at 65° C. More NaOCl solution (50 mL) was added and the mixture was transferred to a container containing 2 kg of ice. A 20 gram portion of finely ground sodium chloride was added, and the mixture was stirred for 20 minutes. The resulting white precipitate of disulfonic acid was filtered off, washed with saturated sodium chloride solution, and then dissolved in water (2 L). An aqueous solution containing 6 percent by weight potassium permanganate was added to the solution at 20° C. until a permanent light pink color was achieved. The mixture was filtered, and sodium chloride (80 g) was added to the filtrate at 50° C. in portions. The mixture was then stirred at 10° C. for 2 hours. The resulting precipitate was filtered off, washed with acetone, and then dried. The yield of disodium 4.4'-dinitrobibenzyl-2,2'-disulfonate was 64 grams.

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