3-Hydroxybenzaldehyde → 3-(Morpholinomethyl)phenol

To a solution of 3-hydroxybenzaldehyde (1 g, 8.19 mmol) in methanol (15 mL) was added morpholine (1.42 g, 16.4 mmol). Then the mixture was stirred at room temperature for 1 h. The mixture was cooled to −5° C., and sodium borohydride (403 mg, 10.6 mmol) was added in small portions. The resulting mixture was stirred at room temperature for 4 h. The mixture was quenched with diluted hydrochloride acid and concentrated. The aqueous solution was washed with ethyl acetate and then made basic by addition of ammonium hydroxide. The basic aqueous slurry was extracted with ethyl acetate and this organic layer was dried and concentrated to give 3-(morpholinomethyl)phenol (0.76 g, 48.2%) as white solid. LCMS retention time 0.871 min, LCMS MH+ 194.

1. temperatureThe mixture was cooled to −5° C.
2. stirringThe resulting mixture was stirred at room temperature for 4 h
3. customThe mixture was quenched with diluted hydrochloride acid
4. concentrationconcentrated
5. washThe aqueous solution was washed with ethyl acetate
6. additionmade basic by addition of ammonium hydroxide
7. extractionThe basic aqueous slurry was extracted with ethyl acetate
8. customthis organic layer was dried
9. concentrationconcentrated

ORD record

ord-805caa3e421548b8b68bd9c7065348c0

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359359B2