反应详情

温度

100 °C

A mixture of 4-hydroxy-3-methoxybenzoic acid (4.5 g, 26.8 mmol), 3-morpholinopropyl chloride (9.5 g, 58.0 mmol), (prepared according to J. Am. Chem. Soc. 1945, 67, 736), potassium carbonate (8.0 g, 58 mmol), potassium iodide (1.0 g, 0.22 mmol) and DMF (80 ml) was stirred and heated at 100° C. for 3 hours. The solid was removed by filtration and the volatiles were removed by evaporation. The residue was dissolved in ethanol (50 ml), 2M sodium hydroxide (50 ml) was added and the mixture heated at 90° C. for 2 hours. After partial evaporation, the mixture was acidified with concentrated hydrochloric acid, washed with ether and then subjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with a gradient of methanol (0 to 25%) in hydrochloric acid (pH2). Partial evaporation of the solvents and lyophilisation gave 3-methoxy-4-(3-morpholinopropoxy)benzoic acid (8.65 g, 97%).

1. customThe solid was removed by filtration
2. customthe volatiles were removed by evaporation
3. dissolutionThe residue was dissolved in ethanol (50 ml)
4. addition2M sodium hydroxide (50 ml) was added
5. temperaturethe mixture heated at 90° C. for 2 hours
6. customAfter partial evaporation
7. washwashed with ether
8. customsubjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column
9. washeluting with water
10. customPartial evaporation of the solvents and lyophilisation