Methyl Decanoate → Vanillyl decanoate

HRID 1056461Notes

Reaction equation

HRID 1056461 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(O)[C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1>CC(C)=O>[C:3]([O:2][CH2:1][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1)(=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8050Methyl DecanoateHCID 62348Vanillyl alcohol

Product 1

HCID 15979852Vanillyl decanoateYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was synthesized by the method described in Kobata et al. (Biosci. Biotechnol. Biochem., 66(2), 319-327, 2002). Decanoic acid methyl ester (2.13 mL, 10.5 mmol), vanillyl alcohol (1.62 g, 10.5 mmol), molecular sheaves 4 Å (10 g), and Novozyme 435 (2.5 g) were added to acetone (50 mL) and stirred for 2 hours at room temperature. The reaction solution was filtered through cellite and the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel chromatography, yielding 2.25 g (7.30 mmol, 73.0 percent) of vanillyl decanoate in the form of a colorless oily substance.

Workup

  1. customThis compound was synthesized by the method
  2. filtrationThe reaction solution was filtered through cellite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe concentrated residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-11ad05997a0a4c39bef970dce0378f1a
Source dataset
uspto-grants-2016_07
Patent number
US09399030B2

Reaction notes

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