Hydrochloric Acid → 2-Chloro-4-hydroxybenzaldehyde

Temperature

-78 °C

Diisobutylaluminium hydride (1M in hexane, 240 mL, 240 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (15 g, 97.7 mmol) in tetrahydrofuran (200 mL), cooled to −78° C., and the mixture was stirred at this temperature for 1 hour then at room temperature for 18 hours. The mixture was then cooled to 0° C. and 1M hydrochloric acid (80 mL) was added dropwise. The reaction mixture was diluted with water (200 mL) and filtered, washing through with ethyl acetate (×2). The layers of the filtrate were separated and the organic solution was dried over magnesium sulfate and concentrated in vacuo, Trituration of the residue with dichloromethane afforded the title compound as a solid in 84% yield, 12.92 g.

1. waitat room temperature for 18 hours
2. temperatureThe mixture was then cooled to 0° C.
3. filtrationfiltered
4. washwashing through with ethyl acetate (×2)
5. customThe layers of the filtrate were separated
6. dry with materialthe organic solution was dried over magnesium sulfate
7. concentrationconcentrated in vacuo, Trituration of the residue with dichloromethane

ORD record

ord-c313e2d1704e4c73b535bf06c521e628

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076356B2