Hydrochloric Acid → 3-Cyclobutyl-2-hydroxybenzaldehyde

1-cyclobutyl-2-methoxymethoxybenzene (1.18 g) was dissolved in tetrahydrofuran (11 mL), and a 1.01M s-butyllithium-cyclohexane solution (8.7 mL) was added to the solution at −60° C. over 15 minutes under an argon gas flow, and then the mixture was stirred for 2 hours. N,N-dimethylformamide (0.90 mL) was added and the mixture was stirred at the same temperature for 2 hours. 4N hydrochloric acid (15 mL) was added at room temperature, and then the mixture was stirred at 60° C. for 20 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain the title compound (0.95 g) as a colorless oily substance.

1. stirringthe mixture was stirred at the same temperature for 2 hours
2. stirringthe mixture was stirred at 60° C. for 20 hours
3. distillationThe solvent was distilled off under reduced pressure and water
4. additionwas added
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. distillationThe solvent was distilled off under reduced pressure
9. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

ORD record

ord-811064359e414a17992bb83b0e85e44c

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367843B2