4-Hydroxybenzaldehyde → 4-(2-Morpholinoethoxy)benzaldehyde

To a solution of 4-hydroxybenzaldehyde (4.04 g, 33.08 mmol), in acetonitrile (50 ml) was added K2CO3 (10.1 g), followed by N-(2-chloroethyl)morpholine hydrochloride (6.16 g). The reaction mixture was heated to reflux overnight, additional N-(2-chloroethyl)morpholine hydrochloride (0.6 g) and K2CO3 (0.5 g) were added and the mixture was refluxed for another 3 hours. The reaction mixture was cooled to room temperature, filtered, and the filtrate was treated with DARCO®, filtered and the solvent was stripped. The residue was partitioned between saturated NaHCO3 (150 ml) and ethyl acetate (300 ml). The layers were separated and the organic layer was washed with 1N NaOH, dried over MgSO4, filtered and stripped to afford, as an amber oil, 6.41 g of 4-[2-(4-morpholinyl)ethoxy]benzaldehyde.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux overnight
3. temperaturethe mixture was refluxed for another 3 hours
4. filtrationfiltered
5. additionthe filtrate was treated with DARCO®
6. filtrationfiltered
7. customThe residue was partitioned between saturated NaHCO3 (150 ml) and ethyl acetate (300 ml)
8. customThe layers were separated
9. washthe organic layer was washed with 1N NaOH
10. dry with materialdried over MgSO4
11. filtrationfiltered

ORD-Eintrag

ord-c9ba254f97be4014844008c2051d0a6b

Quelldatensatz

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05958929