3-Hydroxybenzaldehyde → 3-(2-Morpholin-4-ylethoxy)benzaldehyde

To a solution of 3-Hydroxybenzaldehyde (3.05 g, 24.97 mmol) in acetonitrile (15 ml) was added K2CO3 (7.6 g), followed by N-(2-chloroethyl)morpholine hydrochloride (4.65 g). The reaction mixture was stirred at room temperature for 30 minutes, then at reflux overnight. Additional N-(2-chloroethyl)morpholine hydrochloride (0.93 g) and K2CO3 (0.7 g) were added and the mixture was refluxed for an additional 6 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate was concentrated in vacuo. The residue was partitioned between water and chloroform, the layers were separated and the aqueous layer was extracted with chloroform (2×75 ml). The organic layers were combined, washed with brine, dried over MgSO4, filtered and stripped to afford 7.3 g of 3-[2-(4-morpholinyl)ethoxy]benzaldehyde, as an amber liquid.

1. temperatureat reflux overnight
2. temperaturethe mixture was refluxed for an additional 6 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. filtrationfiltered
5. concentrationthe filtrate was concentrated in vacuo
6. customThe residue was partitioned between water and chloroform
7. customthe layers were separated
8. extractionthe aqueous layer was extracted with chloroform (2×75 ml)
9. washwashed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered

ORD record

ord-acd3c7c93939403da5a46fc3d9368dea

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05958929