1-Decanol → HCID 101083223, compound

HRID 1616717Notes

Reaction equation

HRID 1616717 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12](O)(=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1

Participants

6

Reactant 4

HCID 81741-DecanolHCID 11776TriphenylphosphineHCID 445858Ferulic AcidHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 101083223HCID 101083223, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Decanol (1.58 g, 10.0 mmol), ferulic acid (1.94 g, 10.0 mmol) and triphenylphosphine (2.88 g, 11.0 mmol) were dissolved in THF (20 ml), and DIAD (40% solution of diisopropyl azodicarboxylate in toluene, 5.56 g, 11.0 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 16 hr and concentrated under reduced pressure. Ethyl acetate (100 ml) was added to the residue, and the mixture was washed with 5% aqueous citric acid solution (25 ml×3) and saturated brine (25 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was developed by PTLC (n-hexane:ethyl acetate=2:1), and silica gel containing the object product was stirred with ethyl acetate (100 ml) for 30 min for extraction. The silica gel was filtered off, and the filtrate was concentrated under reduced pressure to give n-decanyl ferulate (2.55 g, yield 76.2%) as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate (100 ml) was added to the residue
  3. washthe mixture was washed with 5% aqueous citric acid solution (25 ml×3) and saturated brine (25 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationMagnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. stirringwas stirred with ethyl acetate (100 ml) for 30 min for extraction
  8. filtrationThe silica gel was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a73c54b2bcd4ee585f5a5338ab60a21
Source dataset
uspto-grants-2014_07
Patent number
US08765809B2

Reaction notes

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