2,6-Lutidine → 4-Acetoxypentanal

HRID 376167Notes

Reaction equation

HRID 376167 reaction equation
[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][C:8](Cl)=[O:9])(=[O:3])[CH3:2].N1C(C)=CC=CC=1C>[Pd].O1CCCC1>[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][CH:8]=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 79372,6-LutidineHCID 543443094-Acetoxypentanoic acid chloride

Product 1

HCID 111054874-Acetoxypentanal

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

45.0 g (0.25 mol) of 4-acetoxypentanoic acid chloride are dissolved in 450 ml of abs. tetrahydrofuran. Then 31.9 ml (0.27 mol) of 2,6-lutidine and 9 g of 5% Pd/C are added and hydrogenation is carried out for 1 hour at 10°-15° C. Upon cessation of hydrogenation, the catalyst and the 2,6-lutidine are removed by filtration and the filtrate is concentrated by evaporation. Distillation of the residue gives 4-acetoxypentanal as a colourless liquid of b.p.34 98°-100° C.

Workup

  1. customUpon cessation of hydrogenation, the catalyst and the 2,6-lutidine are removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-f4fd50062c5e4ab68269608c1a450b82
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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