1-Bromopentane → HCID 19363254, compound

Temperature

90 °C

3-Hydroxy-4-methoxybenzoic acid (9.6 g, 0.057 mol) was dissolved in DMF (90 ml), and to this solution were successively added 1-bromopentane (25.9 g, 0.17 mol, 3.0 eq) and anhydrous potassium carbonate (47.4 g, 0.34 mol, 6.0 eq). The mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and anhydrous potassium carbonate was filtered off. Water (200 ml) was added to the filtrate, and the mixture was extracted twice with ethyl acetate (200 ml). The organic layers were combined, washed with saturated brine (300 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1) to give pentyl 4-methoxy-3-pentyloxybenzoate (17.4 g, 98.8%) as a colorless oil.

1. temperatureThis reaction mixture was cooled to room temperature
2. filtrationanhydrous potassium carbonate was filtered off
3. additionWater (200 ml) was added to the filtrate
4. extractionthe mixture was extracted twice with ethyl acetate (200 ml)
5. washwashed with saturated brine (300 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe drying agent was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1)

ORD record

ord-e287a517e8904dadb9c6b21ed58af1aa

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919