Cumene → Benzenebutanoic acid, 4-(1-methylethyl)-gamma-oxo-

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Reaction Steps

To a suspension of aluminum (III) chloride (6.7 g, 50.1 mmol) and succinic anhydride (2 g, 20 mmol) in 1,2-dichloroethane was added Cumene (2 g, 16.7 mmol) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours, diluted with 20 mL of aqueous HCl solution (1 M) and extracted with ethyl acetate (3×80 mL). The combined organic phases were washed with saturated sodium chloride (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica-gel (4×20 cm, petroleum ether:ethyl acetate=8:1 elution) to give 3.1 g of compound 76. 1H NMR (CDCl3, 300 MHz) δ 1.27-1.29 (d, 6H), 2.80-2.84 (t, 2H), 2.95-3.00 (m, 1H), 3.29-3.33 (t, 2H), 7.32-7.34 (d, 2H), 7.92-7.94 (d, 2H). MS m/z 221 (M+H)+.

Provenance & Evidence