Hydrochloric Acid → 4-Benzyloxy-2-hydroxybenzaldehyde

To a solution of 2,4-dihydroxybenzaldehyde (50.0 g, 362 mmol) in acetonitrile (350 ml) were added sodium hydrogen carbonate (34.6 g, 412 mmol), potassium iodide (6.0 g, 36 mmol), and benzyl chloride (54.0 ml, 470 mmol), and the resulting mixture was refluxed for 24 hours under a nitrogen atmosphere. At the end of the reaction, 1N hydrochloric acid (400 ml) was added, and the resulting mixture was extracted with ethyl acetate (400 ml×2). The organic layer was washed successively with 3% aqueous potassium carbonate solution (300 ml×2), water (300 ml×1), 1N hydrochloric acid (300 ml×1) and saturated aqueous sodium chloride solution (300 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was recrystallized from a mixture of t-butyl methyl ether and hexane to afford the title compound (45.9 g, yield: 56%) as pale orange crystals.

1. temperaturethe resulting mixture was refluxed for 24 hours under a nitrogen atmosphere
2. additionwas added
3. extractionthe resulting mixture was extracted with ethyl acetate (400 ml×2)
4. washThe organic layer was washed successively with 3% aqueous potassium carbonate solution (300 ml×2), water (300 ml×1), 1N hydrochloric acid (300 ml×1) and saturated aqueous sodium chloride solution (300 ml×1)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford the crude product
9. customThe crude product was recrystallized from a mixture of t-butyl methyl ether and hexane

ORD record

ord-063195aff09549ee8e0feaf07aaf6768

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504437B2