Sodium Chloride → 6-Methoxy-2-naphthaldehyde

Temperature

-78 °C

To a solution of 2-bromo-6-methoxynaphthalene (4.00 g, 16.87 mmol) in 100 mL of anhydrous THF under nitrogen atmosphere at -78° C. was added a 1.6M solution of n-butyllithium in hexane (10.6 mL, 16.96 mmol). The reaction mixture turned into a yellow suspension 5 minutes after the addition of butyllithium. The suspension was stirred at -78° C. for 1 hour and then warmed to -23° C. Anhydrous N,N-dimethylformamide (4.0 mL, 51.7 mmol) was added. The reaction mixture was stirred at -23° C. for 30 minutes. Saturated sodium chloride solution (50 mL) was added to quench the reaction. The organic layer was collected and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried with anhydrous magnesium sulphate, filtered, and concentrated under reduced pressure. The residue oil was chromatographed by 10% ethyl acetate in hexanes on silica gel to give 2.86 g (91%) of 6-methoxy-2-naphthaldehyde as a white solid. 1HNMR (300 MHz, CDCl3) δ10.10 (1H, s), 8.26 (1H, s), 7.95-7.78 (3H, m), 7.28-7.18 (2H, m), 3.97 (3H, s).

1. customturned into a yellow suspension 5 minutes
2. temperaturewarmed to -23° C
3. stirringThe reaction mixture was stirred at -23° C. for 30 minutes
4. customto quench
5. customthe reaction
6. customThe organic layer was collected
7. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
8. dry with materialThe combined organic layers were dried with anhydrous magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue oil was chromatographed by 10% ethyl acetate in hexanes on silica gel

ORD record

ord-765fc4becbb848099e6d4d28b49466fa

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554767