Sulfuric Acid → 4-(Chloromethyl)benzaldehyde

Under an argon atmosphere, 4-chloromethylbenzoic acid (15.08 g, 88.40 mmol) was dissolved in THF (150 ml), and 1M borane-THF complex (135 ml, 135.00 mmol) was slowly added dropwise under ice-cooling. The mixture was stirred at room temperature for 2 hours, 1N sulfuric acid (160 ml) was added, and the mixture was stirred for 1 hour and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was dissolved in dichloromethane (300 ml). Manganese dioxide (76.94 g, 885.0 mmol) was added, and the mixture was stirred overnight at room temperature. After filtration through celite, the filtrate was concentrated under reduced pressure to give the title compound (11.93 g, 87%).

1. addition1M borane-THF complex (135 ml, 135.00 mmol) was slowly added dropwise under ice-
2. temperaturecooling
3. stirringthe mixture was stirred for 1 hour
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe obtained crude product
9. stirringthe mixture was stirred overnight at room temperature
10. filtrationAfter filtration through celite
11. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-64f455a07a504fa383a0ce620bf23037

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517996B2