Acetic Acid → HCID 20254624, compound

HRID 2412839Notes

Reaction equation

HRID 2412839 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.[H][H].[C:33](O)(=[O:35])[CH3:34]>[Pd]>[C:33]([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:35])[CH3:34]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24247Perchloric AcidHCID 132762366-(11-Hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 20254624HCID 20254624, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 6-(11-hydroxy-1-oxoundecyl)-2,3-dimethoxy-5-methylphenol (14 g) in acetic acid (200 ml) are added 5% palladium-on-carbon (50% hydrous) (3 g) and 70% perchloric acid (0.1 ml), and catalytic reduction is carried out at atmospheric temperature and pressure. When the hydrogen has ceased to be absorbed, 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 a 5% aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate. The solvent is then distilled off to obtain a colorless oil of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methylphenol (15 g).

Workup

  1. customto be absorbed
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. extractionThe residue is extracted with dichloromethane
  5. washthe dichloromethane layer is washed with a 5% aqueous solution of sodium hydrogen carbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is then distilled off

Sources & evidence

ORD record
ord-d2e8c95e4ee44144a89b5834af3bb39c
Source dataset
uspto-grants-1985_01
Patent number
US04495104

Reaction notes

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