Protocatechuic Acid → Pentyl 3,4-dipentyloxybenzoate

Temperature

110 °C

3,4-Dihydroxybenzoic acid (462 mg, 3 mmol) was dissolved in DMF (10 ml). Potassium carbonate (3.73 g, 27 mmol, 9 eq) and 1-bromopentane (1.70 ml, 13.5 mmol, 4.5 eq) were successively added to this solution at room temperature, and the mixture was stirred at 110° C. for 24 hours. This reaction mixture was filtered, and the residual potassium carbonate was washed with ethyl acetate (50 ml). The filtrate was washed with water (15 ml×3) and saturated brine (15 ml). The organic layer was dried over anhydrous sodium sulfate. After the drying agent was filtered off; the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (heaxane/ethyl acetate=95/5) to give pentyl 3,4-dipentyloxybenzoate (912 mg, 83%).

1. filtrationThis reaction mixture was filtered
2. washthe residual potassium carbonate was washed with ethyl acetate (50 ml)
3. washThe filtrate was washed with water (15 ml×3) and saturated brine (15 ml)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationAfter the drying agent was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe obtained residue was purified by column chromatography (heaxane/ethyl acetate=95/5)

ORD record

ord-8d7d07fc22994ea4a563aa403519e15e

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919