Nitrobenzene → Benzenebutanoic acid, 4-propyl-

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Reaction Steps

To a solution of propylbenzene (14.6 g, 121.4 mmol) in 243 mL of a solution of aluminum chloride in nitrobenzene (1.0M, 243 mmol) was added succinic anhydride (12.15 g, 121.4 mmol). After 3 h, the reaction was quenched with 2N hydrochloric acid, diluted with ether and washed 5 times with dilute hydrochloric acid. The organics were then extracted three times with dilute sodium hydroxide and the combined aqueous layers washed three times with ether. The aqueous layer was then acidified with concentrated hydrochloric acid and extracted twice with ether. The combined ether layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give a brown free flowing solid. This product was disolved in 250 mL of acetic acid and ~1 g of Pearlman's catalyst was added. The mixture was stirred vigorously under 1 atmosphere of hydrogen for 16 h, filtered through a pad of celite and concentrated in vacuo. The product was diluted with toluene and concentrated in vacuo to remove the remaining acetic acid to afford 19.3 g of the title compound as a pale-tan crystalline solid: 400 MHz 1H NMR (CDCl3) δ 7.08 (s, 4H), 2.7-2.3 (m, 6H), 1.94 (m, 2H), 1.62 (m, 2H), 0.93 (t, 3H).

Provenance & Evidence