Vanillin → n-Hexyl vanillate

HRID 1902170Notes

Reaction equation

HRID 1902170 reaction equation
[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]=1

Participants

5

Reactant 4

HCID 1183VanillinHCID 6101p-Toluenesulfonic acidHCID 81031-HexanolHCID 8468Vanillic Acid2×

Product 1

HCID 128609n-Hexyl vanillateYield 86%

Procedure

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.

Workup

  1. customAfter the unreacted alcohol was removed by distillation in a vacuum
  2. distillationthe hexyl vanillate was distilled
  3. customobtained in 86% yield

Sources & evidence

ORD record
ord-af51c178620a4dae801724fedddac988
Source dataset
uspto-grants-1982_12
Patent number
US04362510

Reaction notes

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