Sodium Hydroxide → HCID 19363244, compound

Pentyl 4-methoxy-3-pentyloxybenzoate (17.4 g, 0.056 mol) was dissolved in methanol (85 ml). A 1N aqueous sodium hydroxide solution (85 ml, 0.085 mol, 1.5 eq) was added, and the mixture was refluxed under heating for 1.5 hours. This reaction mixture was cooled to room temperature, and washed with n-hexane (100 ml). A 10% aqueous hydrochloric acid solution (ca. 120 ml) was added to the aqueous layer under ice-cooling to make the same acidic. This was extracted twice with ethyl acetate (220 ml). The organic layers were combined, washed with saturated brine (400 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 recryst azation from ethyl acetate to give 4-methoxy-3-pentyloxybenzoic acid (10.7 g, 79.6%) as colorless crystals.

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 1.5 hours
3. washwashed with n-hexane (100 ml)
4. additionA 10% aqueous hydrochloric acid solution (ca. 120 ml) was added to the aqueous layer under ice-
5. temperaturecooling
6. extractionThis was extracted twice with ethyl acetate (220 ml)
7. washwashed with saturated brine (400 ml)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe drying agent was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe obtained residue was purified by recryst azation from ethyl acetate

ORD record

ord-8ab808802be74025b4c8403993b97b66

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919