Hydrochloric Acid → 2-Hydroxy-4-(trifluoromethyl)benzaldehyde

To a solution of p-trifluoromethylphenol (7.1 g, 44 mmol) and 2,6-lutidine (1.9 g, 17.6 mmol) in toluene (80 mL) was slowly added SnCl4 (1.2 g, 4.4 mmol). The solution was stirred at room temperature for 20 minutes. Paraformaldehyde was added (3.2 g, 106 mmol) and the reaction was stirred at 110° C. for 12 hours. After cooling to room temperature, the reaction mixture was poured into water (250 mL), and adjusted to pH 1 with concentrated HCl. The mixture was extracted with diethyl ether (500 mL), and the organic layer was washed twice with saturated brine and dried over Na2SO4. The solvent was removed by rotary evaporation to leave a yellow oil. The oil was loaded onto a silica gel column and eluted with 6:1 hexane:ethyl acetate. The yield of product was 1.0 g (12%). 1H NMR (CDCl3): δ 7.21-7.91 (m, 12H), 9.91 (s, 1H), 11.32 (s, 1H).

1. stirringthe reaction was stirred at 110° C. for 12 hours
2. temperatureAfter cooling to room temperature
3. extractionThe mixture was extracted with diethyl ether (500 mL)
4. washthe organic layer was washed twice with saturated brine
5. dry with materialdried over Na2SO4
6. customThe solvent was removed by rotary evaporation
7. customto leave a yellow oil
8. washeluted with 6:1 hexane

ORD record

ord-1f10096e7b9b429f986275be693e5f47

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576779B1