反应详情

Dissolved 1.2 g (4 mmol) of 6-Hydroxymethyl-2-naphthalenecarboxylic acid benzyl ester in 100 ml of CH2Cl2, slowly added 5.2 g of MnO2 (60 mmol) and stirred at room temperature for 2 hours, then filtered through Ceilite. The Celite was washed with CH2Cl2 and combined organics taken to dryness. The oily residue was solidified with EtOAc/Hexanes (1:1) and collected by vacuum filtration, washed with small amount of methanol, dried to get 1.2 g of 6-Formyl-2-naphthalenecarboxylic acid benzyl ester. 1H NMR (400 MHz, DMSO-d6): δ 10.192 (s, 1H, —CHO), 8.754 (s, 1H, Ar—H), 8.667 (s, 1H, Ar—H), 8.327(t, J=9.4, 2H, Ar—H), 8.142(dd, J=1.6&7.0 Hz, 1H, Ar—H), 7.987-7.962 (dd, J=1.6&7.0 Hz, 1H, Ar—H), 7.544-7.526 (m, 2H, Ar—H), 7454-7.375 (m, 3H, Ar—H), 5.442 (s, 2H, —COOCH2—), MS m/e 289[M+−1].

1. filtrationfiltered through Ceilite
2. washThe Celite was washed with CH2Cl2
3. filtrationcollected by vacuum filtration
4. washwashed with small amount of methanol
5. customdried