Benzene → HCID 54082787, compound

HRID 267317Notes

Reaction equation

HRID 267317 reaction equation
[CH3:1][C:2](=[CH:7][C:8]#[C:9][C:10]([CH3:23])=[CH:11][CH:12]=[C:13]1[C:18]([CH3:20])([CH3:19])[CH2:17][C:16](=[O:21])[CH:15]=[C:14]1[CH3:22])[CH:3]=[CH:4][CH:5]=[O:6].C1C=CC=CC=1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CC(C)=O>[CH3:1][C:2](=[CH:7][CH:8]=[CH:9][C:10]([CH3:23])=[CH:11][CH:12]=[C:13]1[C:18]([CH3:20])([CH3:19])[CH2:17][C:16](=[O:21])[CH:15]=[C:14]1[CH3:22])[CH:3]=[CH:4][CH:5]=[O:6]

Participants

6

Reactant 3

HCID 241BenzeneHCID 7047QuinolineHCID 54455634HCID 54455634, compound

Product 1

HCID 54082787HCID 54082787, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 180AcetoneSolvent

Procedure

2 g. of pure 4,8-dimethyl-10-(4-oxo-2,6,6-trimethyl-2-cyclohexenylidene)-2,4,8-decatrien-6-ynal in 50 ml. of benzene was hydrogenated in the presence of 0.5 g. of Lindlar catalyst and 0.5 ml. of a 1% solution of quinoline in acetone. After consumption of 240 ml. of hydrogen, which took place within 21/2 hours, the suspension was filtered and concentrated. The residue crystallized only partially after chromatography on 200 g. of silica gel G with benzene ethyl ether in a volume ratio of 3:2.

Workup

  1. customAfter consumption of 240 ml
  2. custom2 hours
  3. filtrationthe suspension was filtered
  4. concentrationconcentrated
  5. customThe residue crystallized only partially after chromatography on 200 g

Sources & evidence

ORD record
ord-8e94fe89636d4edda79140f21a0b0c03
Source dataset
uspto-grants-1976_03
Patent number
US03941841

Reaction notes

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