Quinoline → 3-Buten-2-ol, 1,1-dimethoxy-2-methyl-

HRID 1764561Notes

Reaction equation

HRID 1764561 reaction equation
[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]([CH3:8])([OH:7])[C:5]#[CH:6].N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd]>[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]([CH3:8])([OH:7])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 128752274,4-Dimethoxy-3-methyl-but-1-yn-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 110080503-Buten-2-ol, 1,1-dimethoxy-2-methyl-

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

198 G. of 4,4-dimethoxy-3-methyl-but-1-yn-3-ol are dissolved in 960 ml. of high-boiling petroleum ether and, after the addition of 19.35% palladium catalyst and 19.3 g. of quinoline, hydrogenated under normal conditions. After the uptake of 33.5 l. of hydrogen, the hydrogenation is stopped. The catalyst is filtered off. The filtrate is evaporated under reduced pressure. The remaining 4,4-dimethoxy-3-methyl-but-1-en-3-ol boils, after rectification, at 70°-72° C./18 mm Hg.

Workup

  1. filtrationThe catalyst is filtered off
  2. customThe filtrate is evaporated under reduced pressure
  3. customat 70°-72° C.

Sources & evidence

ORD record
ord-e76f93dd4ca34e539ed05c2321c99da9
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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