Vanillin → n-Hexyl vanillate
Reaktionsgleichung
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(O)(=O)[C:13]1[CH:21]=[CH:20][C:18](O)=[C:15]([O:16]C)[CH:14]=1.C(O)CCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:2]([O:16][CH2:15][CH2:14][CH2:13][CH2:21][CH2:20][CH3:18])(=[O:1])[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1Komponenten
5
Versuchsvorschrift
Hexyl vanillate was synthesized according to the method of Pearl, I.A., and McCoy, J. F. "Reaction of Vanillin and its Derived Compounds. Some Esters of Vanillic Acid." J. AM. CHEM. SOC. 69: 3071 (1947). Vanillic acid (20.2 g, 0.12 mol) was refluxed with n-hexanol (29.9 ml, 0.24 mol) in the presence of p-toluenesulfonic acid (0.2 g) for 26 hours. After the unreacted alcohol was removed by distillation in a vacuum, the hexyl vanillate was distilled and obtained in 86% yield.