HCID 20386045, compound → 4-[4-Acetyl-7-(1-hydroxycyclohexyl)heptyl]benzoic Acid

HRID 26604Notes

Reaction equation

HRID 26604 reaction equation
[C:1]([CH:4]([CH2:17][C:18]#[C:19][C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pt]>[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][C:20]1([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 20386045HCID 20386045, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 203861024-[4-Acetyl-7-(1-hydroxycyclohexyl)heptyl]benzoic Acid

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-Acetyl-7-(1-hydroxycyclohexyl)-6-heptyn-1-yl]benzoic acid (5.1 g., 0.014 mole) in ethyl acetate (55 ml.) is hydrogenated over 2.0 g. of a 5% Pt on charcoal catalyst at 1 atmosphere pressure and room temperature. The theoretical amount of hydrogen (0.028 mole) is absorbed in 25 minutes. The catalyst is filtered off, the solvent is evaporated and the residue (5 g.) is chromatographed on 75 g. of silica gel with 2% methanol in chloroform as eluant. 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. customthe solvent is evaporated
  4. customthe residue (5 g.) is chromatographed on 75 g

Sources & evidence

ORD record
ord-e1514bf358c64722a627226badf5c860
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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