4-Hydroxybenzaldehyde → 4-(4-Hydroxybutoxy)benzaldehyde

Temperature

120 °C

In a 1 L three neck distillation flask, p-hydroxybenzaldehyde (24.4 g, 20 mmol), 4-chlorobutylacetate (36.1 g, 240 mmol), potassium carbonate (33.2 g, 240 mmol) and dimethylformamido (150 ml) were placed and stirred for 3 hours at 120° C. After the reaction mixture was cooled, water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was dissolved in methanol (100 ml), and potassium hydroxide (22.4 g, 0.4 mmol) dissolved in water (50 ml) was dropwise added to the solution. The mixture was refluxed for 2 hours, and then cooled. Water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was purified through column chromatography to prepare the titled compound (35.3 g, yield: 91%).

1. temperatureAfter the reaction mixture was cooled
2. extractionthe resulting mixture was extracted with ethyl acetate
3. customThe solvent was removed
4. customto obtain an oily product
5. additionwas dropwise added to the solution
6. temperatureThe mixture was refluxed for 2 hours
7. temperaturecooled
8. extractionthe resulting mixture was extracted with ethyl acetate
9. customThe solvent was removed
10. customto obtain an oily product
11. customThe product was purified through column chromatography

ORD record

ord-0bb5a73b95004131be314b9f5bcd5029

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06461694B1