Morpholine → 3-Methoxy-4-(morpholinomethyl)phenol

Participants

Reaction Steps

A mixture of 4-hydroxy-2-methoxybenzaldehyde (1.0 g, 6.57 mmol) and morpholine (2.0 g, 23.0 mmol) in 50 ml dichloroethane was stirred at rt for 1 h. Sodium triacetoxyborohydride (2.0 g, 9.44 mmol) was added in portions over 20 minutes. The reaction mixture was stirred at rt over night. Aqueous NaHCO3 (sat.) was added, the phases were separated and the aqueous phase was extracted with DCM once. The solvent was removed by evaporation and the residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent. There was obtained 1.19 g (81%) of 7A iii as a solid. 1H NMR (500 MHz, CDCl3): δ 2.41-2.71 (m, 4H), 3.52 (s, 2H), 3.72 (s, 3H), 3.69-3.79 (m, 4H), 6.27 (d, 1H), 6.32 (s, 1H), 7.10 (d, 1H).

Provenance & Evidence