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

HRID 904454Notes

Reaction equation

HRID 904454 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-6257e5bac30e416ba14124dd05da3b04
Source dataset
uspto-grants-1980_10
Patent number
US04230872

Reaction notes

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