HCID 21397410, compound → HCID 21397373, compound

HRID 1439478Notes

Reaction equation

HRID 1439478 reaction equation
[C:1]([C:4]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH2:14][CH2:15][CH2:16][CH:17]([O:23]CC1C=CC=CC=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]>CCO.[Pd]>[C:1]([C:4]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH2:14][CH2:15][CH2:16][CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 21397410HCID 21397410, compound

Product 1

HCID 21397373HCID 21397373, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-Acetyl-8-phenyl-12-benzyloxyheptadecanoic acid (1.42 g., slightly impure) is dissolved in EtOH (50 ml.), and is hydrogenated over 10% palladium on carbon at atmospheric pressure and 25° C. The hydrogenation is stopped after 2 hours, the catalyst is filtered off, and the solvent is removed in vacuo to obtain the product as a crude viscous yellowish oil. This oil is chromatographed through a silica gel column (CHCl3) to obtain 8-acetyl-8-phenyl-12-hydroxyheptadecanoic acid as a virtually colorless oil (350 ).

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customto obtain the product as a crude viscous yellowish oil
  4. customThis oil is chromatographed through a silica gel column (CHCl3)

Sources & evidence

ORD record
ord-8917d4d90bb7480b9feb857ee08dc15b
Source dataset
uspto-grants-1977_11
Patent number
US04059601

Reaction notes

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