2,6-Lutidine → 4-Ethoxycarbonylmethoxybutanal

HRID 376158Notes

Reaction equation

HRID 376158 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12])=[O:5])[CH3:2].N1C(C)=CC=CC=1C>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 79372,6-LutidineHCID 543801394-Ethoxycarbonylmethoxybutyric acid chloride

Product 1

HCID 189915874-Ethoxycarbonylmethoxybutanal

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

29 g (0.14 mol) of 4-ethoxycarbonylmethoxybutyric acid chloride are dissolved in 290 ml of tetrahydrofuran and the solution is hydrogenated under normal pressure at 10°-15° C. by addition of 5.8 g of 5% Pd/C and 18 ml of 2,6-lutidine. Upon cessation of hydrogenation, the catalyst is removed by filtration and the filtrate is concentrated by evaporation. Distillation of the crude product gives 4-ethoxycarbonylmethoxybutanal as a clear colourless liquid of b.p. 72°-74° C./2.10-2 torr.

Workup

  1. customUpon cessation of hydrogenation, the catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-08dbff0f6fe244dd88fe11bb6c428a1f
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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