Quinoline → 1,2-Benzenediol, 4-(11-hydroxy-1,9-undecadienyl)-, (Z,Z)-

HRID 845802Notes

Reaction equation

HRID 845802 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[C:18][CH2:19][OH:20])[CH:5]=[CH:6][C:7]=1[OH:8].N1C2C(=CC=CC=2)C=CC=1>C(O)C.[Pd]>[OH:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][OH:20])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 10445935HCID 10445935, compound

Product 1

HCID 703630801,2-Benzenediol, 4-(11-hydroxy-1,9-undecadienyl)-, (Z,Z)-Yield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.545 g of the product obtained in Example 7 in 20 ml of absolute ethanol containing 0.1 ml of freshly distilled quinoline was hydrogenated at room temperature and normal pressure using as catalyst 0.136 g of palladium on calcium carbonate (5% Pd; poisoned with lead "Lindlar-catalyst"). After consumption of the theoretical amount of hydrogen, the catalyst was filtered off and the filtrate evaporated in a vacuum. The residue was purified by HPLC with methanol/water (6:4) to yield 0.416 g of the title compound.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter consumption of the theoretical amount of hydrogen
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate evaporated in a vacuum
  5. customThe residue was purified by HPLC with methanol/water (6:4)

Sources & evidence

ORD record
ord-0aeabe900b264fc593882c05f0222474
Source dataset
uspto-grants-1988_07
Patent number
US04760087

Reaction notes

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