Pyridine → Methyl 6-formyl-2-naphthalenecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 5 mL (61.8 mmol) of pyridine and 70 mL of CH2Cl2 was cooled to 0° C. Then 3.0 g (30 mmol) of CrO3 was added in several portions. The mixture was stirred at 0° C. for 15 min before a solution of 0.69 g (3.19 mmol) of methyl 6-hydroxymethyl-2-naphthoate in 10 mL of CH2Cl2 was added. The mixture was stirred at room temperature for 2 hr and then filtered through Florisil (500 mL CH2Cl2 rinse). The filtrate and washings were concentrated and filtered through 50 g of silica gel with 50% EtOAc/hexane to give 0.66 g (96% yield) of the pure aldehyde as a white solid. The analytical sample was recrystallized from EtOAc/hexane: mp 132°-134° C.; IR (mull) 1740, 1700, 1350, 1310, 1270, 1220, 1180, 1140, 1110, 990, 920, 830, 780, 760 cm- 1 ; 1H NMR (CDCl3) δ4.00 (s, 3, CO2CH3), 8.0-8.7 (m, 6, ArH), 10.23 (s, 1, CHO); MS calcd for C13H10O3 214.0630, found 214.0627.

Provenance & Evidence