Quinoline → 1,1-Diethoxy-4-methyl-2,4-hexadien-6-ol

HRID 1729841Notes

Reaction equation

HRID 1729841 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[C:5]#[C:6][C:7]([CH3:11])=[CH:8][CH2:9][OH:10])[CH3:2].N1C2C(=CC=CC=2)C=CC=1>[Pd]>[CH2:13]([O:12][CH:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]([CH3:11])=[CH:8][CH2:9][OH:10])[CH3:14]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 544982151,1-Diethoxy-4-methyl-4-hexen-2-yn-6-ol

Product 1

HCID 544560941,1-Diethoxy-4-methyl-2,4-hexadien-6-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

198 g. of 1,1-diethoxy-4-methyl-4-hexen-2-yn-6-ol are hydrogenated in the usual manner in the presence of 35 g. of a lead/palladium/calcium carbonate catalyst, 5 ml. of quinoline and 1500 ml. of high boiling petroleum ether. There is obtained 1,1-diethoxy-4-methyl-2,4-hexadien-6-ol of boiling point 96°-98° (0.01 mm.); nD20 = 1.4730 - 1.4760.

Sources & evidence

ORD record
ord-b9abc9bc30d74b37a23b157477006817
Source dataset
uspto-grants-1976_11
Patent number
US03989758

Reaction notes

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