Acetic Acid → HCID 20254624, compound

HRID 1903428Notes

Reaction equation

HRID 1903428 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([C:14]1[C:19]([OH:20])=[C:18]([O:21][CH3:22])[C:17]([O:23][CH3:24])=[CH:16][C:15]=1[CH3:25])=O.Cl(O)(=O)(=O)=O.[C:31](O)(=[O:33])[CH3:32]>[Pd]>[C:31]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:14]1[C:19]([OH:20])=[C:18]([O:21][CH3:22])[C:17]([O:23][CH3:24])=[CH:16][C:15]=1[CH3:25])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24247Perchloric AcidHCID 132762366-(11-Hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol

Product 1

HCID 20254624HCID 20254624, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution (200 ml) of 6-(11-hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol (14 g) in acetic acid is added 5% palladium-on-carbon (50% hydrate; 3 g) and 70% perchloric acid (0.1 ml), and catalytic reduction is carried out at ambient temperature and atmospheric pressure. After completion of the absorption of hydrogen, the catalyst is filtered off and the filtrate is concentrated under reduced pressure. The residue is extracted with dichloromethane, and the dichloromethane layer is washed with 5% aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. Removal of the solvent by distillation gives a colorless oil of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methylphenol (15 g).

Workup

  1. customis carried out at ambient temperature
  2. customAfter completion of the absorption of hydrogen
  3. filtrationthe catalyst is filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. extractionThe residue is extracted with dichloromethane
  6. washthe dichloromethane layer is washed with 5% aqueous sodium bicarbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. distillationby distillation

Sources & evidence

ORD record
ord-8e22dc1fdd89451b8dd7bc60f505aebb
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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