Quinoline → HCID 86733102, compound

HRID 267316Notes

Reaction equation

HRID 267316 reaction equation
[CH3:1][C:2]([CH:4]([OH:21])[C:5]#[C:6][C:7]([CH3:20])=[CH:8][CH:9]=[C:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[O:18])[CH:12]=[C:11]1[CH3:19])=[CH2:3].N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C1C=CC=CC=1>[CH3:3][C:2]([CH:4]([OH:21])/[CH:5]=[CH:6]\[C:7]([CH3:20])=[CH:8][CH:9]=[C:10]1[C:15]([CH3:16])([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]=[C:11]1[CH3:19])=[CH2:1]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 53756262HCID 53756262, compound

Product 1

HCID 86733102HCID 86733102, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 241BenzeneSolvent

Procedure

6.5 g. of purified 2,6-dimethyl-8-(4-oxo-2,6,6-trimethyl-2-cyclohexenylidene)-1,6-octadien-4-yn-3-ol was hydrogenated with 1 g. of Lindlar catalyst (a palladium-clacium carbonate catalyst deactivated by the addition of lead and quinoline) in benzene. 700 ml. of hydrogen was consumed within 4 hours. After this period, the catalyst was removed from the solution and the solution was washed with water, then dried and evaporated under reduced pressure. The product was purified by chromatography on 200 g. of silica gel G using petroleum ether and ethyl ether solvent in a volume ratio of 1 to 3. The material was identified as 4-cis-2,6-dimethyl-8-(4-oxo-2,6,6-trimethyl-2-cyclohexenylidene)-1,4,6-octatrien-3-ol).

Workup

  1. customof hydrogen was consumed within 4 hours
  2. waitAfter this period
  3. customthe catalyst was removed from the solution
  4. washthe solution was washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe product was purified by chromatography on 200 g

Sources & evidence

ORD record
ord-d77e34d3787440f590f20444fb072afb
Source dataset
uspto-grants-1976_03
Patent number
US03941841

Reaction notes

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