Citric Acid → 2-Cyclopropoxy-5-(trifluoromethoxy)benzaldehyde

Sulfur trioxide pyridine complex (0.90 g, 5.7 mmol) was added to a solution of 2-cyclopropoxy-5-(trifluoromethoxy)benzenemethanol (Description 13, 393 mg, 1.6 mmol) and triethylamine, (1.54 mL, 11.1 mmol) in dimethylsulfoxide (3 mL) and the mixture was stirred at room temperature for 45 min. Further triethylamine (0.44 mL, 3.2 mmol) and sulfur trioxide pyridine complex (0.126 g, 0.8 mmol) were added and the mixture was stirred at room temperature for 30 min. The mixture was poured into aqueous citric acid (10%, 50 mL) and extracted with ethyl acetate. The combined organic fractions were washed with aqueous citric acid (10%, 3×50 mL) and water (3×50 mL), dried (Na2SO4), and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (0.326 g, 84%). 1H NMR (360 MHz, CDCl3) δ0.86 (4H, m), 3.82-3.9 (1H, m), 7.42 (2H, m), 7.62 (1H, d, J 2.5 Hz), and 10.36 (1H, s).

1. stirringthe mixture was stirred at room temperature for 30 min
2. extractionextracted with ethyl acetate
3. washThe combined organic fractions were washed with aqueous citric acid (10%, 3×50 mL) and water (3×50 mL)
4. dry with materialdried (Na2SO4)
5. customthe solvent was evaporated under reduced pressure

ORD record

ord-3630ad1cb1ba4d1499299aafac4e1f7b

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06214846B1