Hydrochloric Acid → HCID 15143606, compound

Participants

Reaction Steps

Sodium hydride (60% in mineral oil; 1.32 g, 0.33 mol) was washed free of mineral oil by stirring in hexane and decanting the solvent. Tetrahydrofuran (75 mL) was added and the suspension was stirred at 0°. A solution of 2-phenylmethyl1-naphthol (7.00 g, 0.030 mol) in tetrahydrofuran (100 mL) was added dropwise. After the mixture was stirred for two hours, a solution of succinic anhydride (3.30 g, 0.033 mol) in tetrahydrofuran (80 mL) was added dropwise. After stirring for one hour at 0°, 1 N hydrochloric acid was added slowly until the mixture was acidic. The tetrahydrofuran was removed on a rotary evaporator and the residue was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water and brine and was dried over MgSO4. Concentration provided a yellow solid, which was recrystallized (1-chlorobutane) to provide the title compound (6.89 g, 69%) as white crystals: mp 139.5°-140.5°; NMR (CDCl3) 7.79 (m, 2H), 7.66 (d, J=7 Hz, IH), 7.47 (m, 2H), 7.3-7.2 (m, 6H), 4.02 (s, 2H), 3.01 (t, J=6 Hz, 2H), 2.81 (t, J=6 Hz, 2H); IR (mull) 3200-2400, 1745, 1714; Calcd. for C21H18O4 : C-75.43 H-5.43; Found C-75.13 H-5.42.

Provenance & Evidence