6-(4-Hydroxyphenyl)hexanoic acid → HCID 178525431, compound

HRID 330556Notes

Reaction equation

HRID 330556 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1.[H][H]>C(O)C.[C].[Rh]>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 2473626-(4-Hydroxyphenyl)hexanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 178525431HCID 178525431, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 702EthanolSolvent

Procedure

6-(4-Hydroxyphenyl)hexanoic acid (2 g) is subjected to catalytic reduction in the presence of 5% rhodium-carbon (500 mg) in ethanol (100 ml) at an initial hydrogen pressure of 10.1 kg/cm2. The catalyst is filtered off and the filtrate is concentrated under reduced pressure and subjected to silica gel column chromatography. Elution is carried out with 4% ethanol-chloroform to give three fractions. The first fraction is recrystallized from ether-ligroin to give 392 mg of cis-6-(4-hydroxycyclohexyl)hexanoic acid, m.p. 83°-85° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. washElution
  4. customto give three fractions
  5. customThe first fraction is recrystallized from ether-ligroin

Sources & evidence

ORD record
ord-d36c27c6688141b4833226cae80366f0
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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