Sodium Hydroxide → HCID 11375701, compound

Participants

Reaction Steps

2 g (50 mmol) of sodium hydroxide and 25 ml of methanol (i.e., 25 ml of a 2N solution of methanolic sodium hydroxide) are added to 1 g (1.9 mmol) of methyl 6-[3-adamantan-1-yl-4-(2,2-dimethyl[1,3]dioxolan-4-ylmethoxy)phenyl]naphthalene-2-carboxylate. The reaction medium is heated at the reflux of methanol for 6 h and then at ambient temperature for 2 days and, finally, evaporated to dryness. The solid residue is taken up in water, and the aqueous phase is acidified to pH=2-3 and extracted with ether. The organic phase is washed with water and then with brine, dried over magnesium sulfate, filtered, and evaporated until only approximately 10 ml of a suspension of the product in ether remains. The crystals are then filtered off and dried. After drying, 862 mg (88%) of a yellowish powder are obtained (mp=287° C.). 1H NMR (CDCl3+drop DMSO-d6) (250 MHz): 1.43 (s, 3H), 1.49 (s, 3H), 1.80 (s, 6H), 2.12 (broad s, 3H), 2.18 (s, 6H), 4.05 (m, 2H), 4.16-4.30 (m, 2H), 4.60 (m, 1H), 7.0 (d, J=8.5 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.6 (s, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.89-8.00 (m, 3H), 8.09 (d, J=10.0 Hz, 1H), 8.63 (s, 1H).

Provenance & Evidence