Eugenol → Citrusin C

HRID 1368796Notes

Reaction equation

HRID 1368796 reaction equation
C([O:4][C@H:5]([C@H:8]([C@@H:13]([C@@H:18]([CH2:23][O:24][C:25](=O)[CH3:26])[O:19]C(=O)C)[O:14]C(=O)C)[O:9]C(=O)C)[CH:6]=[O:7])(=O)C.[C:28]1([O:38][CH3:39])[C:29](=[CH:31][CH:32]=[C:33]([CH:37]=1)[CH2:34]C=C)O>C1(C)C=CC=CC=1>[CH3:39][O:38][C:28]1[CH:37]=[C:33]([CH2:32][CH:31]=[CH2:29])[CH:34]=[CH:26][C:25]=1[O:24][C@@H:23]1[O:4][C@H:5]([CH2:6][OH:7])[C@@H:8]([OH:9])[C@H:13]([OH:14])[C@H:18]1[OH:19]

Participants

4

Reactant 2

HCID 3314EugenolHCID 92972D-Glucose, 2,3,4,5,6-pentaacetate

Product 1

HCID 3084296Citrusin CYield 36.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.0 g of glucose pentaacetate were dissolved in 40 ml of absolute toluene, to which 3.28 g of eugenol and 2.0 g of molecular sieves 4A were then added. The mixture was stirred for about one hour. Next, 1 ml of a boron trifluoridediethyl ether complex was added to the mixture. Stirring was further continued for a day and night. After the end of the reaction, molecular sieves 4A was filtered off. The filtrate was washed twice with each 50 ml of a 0.5N aqueous solution of potassium hydroxide to remove unreacted eugenol. After washed further with water and dried with sodium sulfate, it was dried under reduced pressure to obtain 2.4 g of the intended product. According to 13C-NMR of the crystals obtained, a signal of C-1 position was detected at 102.9 ppm. It was, therefore, confirmed that the product had a β-bonding.

Workup

  1. additionwere then added
  2. additionNext, 1 ml of a boron trifluoridediethyl ether complex was added to the mixture
  3. stirringStirring
  4. waitwas further continued for a day and night
  5. filtrationwas filtered off
  6. washThe filtrate was washed twice with each 50 ml of a 0.5N aqueous solution of potassium hydroxide
  7. customto remove unreacted eugenol
  8. washAfter washed further with water
  9. dry with materialdried with sodium sulfate, it
  10. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-6690e3765d534fa1b121bd61aab4e5b4
Source dataset
uspto-grants-2003_06
Patent number
US06576247B1

Reaction notes

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