Formaldehyde → 4-Morpholinobut-2-YN-1-OL

Participants

Reaction Conditions

Reaction Steps

A mixture of formaldehyde (37% in water, 20.7 ml) and morpholine (17.1 ml) was adjusted to pH 3.5 with diluted sulfuric acid. Propargyl alcohol (10 g), potassium iodide (0.3 g), and copper (II) sulfate (0.14 g) were added to the solution and the whole was stirred at 95° C. for 6 hours. After cooling, the insoluble material was removed by filtration and the pH of the filtrate was adjusted to 9 with 24% sodium hydroxide solution. Brine (100 ml) was added to the solution and the solution was extracted with a mixture of ethyl acetate and ethanol (10:1) eight times and then with n-butanol six times. The combined extract was dried over magnesium sulfate and evaporated in vacuo. The residue was distilled in reduced pressure to give 4-morpholino-2-butyn-1-ol (14.03 g).

Provenance & Evidence