反应详情

3-(2-Methoxy-5-methylphenyl)-3-phenylpropionic acid (12.8 g, 0.05 mol) (J. D. Simpson & H. Stehphen, J. Chem. Soc. 1956 1382) and thionyl chloride (50 ml) are heated on a water bath for 3 h. The excess of thionyl chloride is distilled off under reduced pressure. The remaining crude 3-(2-methoxy-5-methylphenyl)3-phenylpropionyl chloride is dissolved in 50 ml of dichloromethane and added dropwise to a stirred solution of diisopropylamine (20.2 g, 0.20 mol) in 200 ml of dichloromethane at about 0° C. The solution is left for 2 h, the solvent is distilled off and the remaining material is treated with water. The solid product consisting of N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropionamide is filtered off, dried and added in small portions to a stirred suspension of lithium aluminium hydride (6.0 g, 0.16 mol) in dry ether (700 ml). The mixture is refluxed for 2 days. Excess of hydride is destroyed by the careful addition of water, the ether layer is separated and dried with anhydrous sodium sulfate. After filtration the solution is added to a solution of excess fumaric acid in ether. The precipitated salt is collected and crystallized from 2-propanol. The hydrogen fumarate melts at 176° C.

1. distillationThe excess of thionyl chloride is distilled off under reduced pressure
2. dissolutionThe remaining crude 3-(2-methoxy-5-methylphenyl)3-phenylpropionyl chloride is dissolved in 50 ml of dichloromethane
3. distillationthe solvent is distilled off
4. additionthe remaining material is treated with water
5. filtrationis filtered off
6. customdried
7. temperatureThe mixture is refluxed for 2 days
8. customExcess of hydride is destroyed by the careful addition of water
9. customthe ether layer is separated
10. dry with materialdried with anhydrous sodium sulfate
11. filtrationAfter filtration the solution
12. additionis added to a solution of excess fumaric acid in ether
13. customThe precipitated salt is collected
14. customcrystallized from 2-propanol