HCID 54351154, compound → 3-[4-(2-Acetyl-6-hydroxyundecyl)phenyl]propionic Acid

HRID 26617Notes

Reaction equation

HRID 26617 reaction equation
[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][C:6]1[CH:16]=[CH:15][C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54351154HCID 54351154, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 203861173-[4-(2-Acetyl-6-hydroxyundecyl)phenyl]propionic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

p-(2-Acetyl-6-hydroxyundecyl)cinnamic acid (2.6 g., 0.0072 mole) in ethanol (30 ml.) is hydrogenated over 0.7 g. of a 5% Pd on charcoal catalyst at 1 atmosphere pressure and room temperature. The theoretical amount of hydrogen (0.0072 mole) is absorbed in 7 minutes. The catalyst is filtered off, solvent removed in vacuo, and the residue chromatographed on 45 g. of silica gel with 2% methanol in chloroform elution. The title compound is obtained as a colorless, viscous oil.

Workup

  1. customat 1 atmosphere pressure and room temperature
  2. filtrationThe catalyst is filtered off
  3. customsolvent removed in vacuo
  4. customthe residue chromatographed on 45 g
  5. washof silica gel with 2% methanol in chloroform elution

Sources & evidence

ORD record
ord-a25e0d4d793142069a5e91f7416d122a
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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