Butanal → Hexanoic acid, 2-cyano-, ethyl ester

HRID 2253716Notes

Reaction equation

HRID 2253716 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH3:4].[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:7].N1CCCCC1.[H][H]>C(O)(=O)C.[Pd]>[CH2:1]([CH:8]([C:6]#[N:7])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 261ButanalHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 98011Hexanoic acid, 2-cyano-, ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

323 g of butyraldehyde and 422 g of ethyl cyanoacetate are dissolved in 750 ml of glacial acetic acid, 15 g of piperidine are added, and the reaction mixture is stirred, during which it warms to about 55° C. After the reaction mixture has been cooled to room temperature, 20 g of 5% Pd-C catalyst are added, and the mixture is then hydrogenated at 30° and an H2 pressure of 2 bar until the calculated amount of hydrogen has been taken up (about 7 hours). After the catalyst has been separated off, the hydrogenation solution is evaporated on a rotary evaporator, the residue is taken up in..methyl tertiary-butyl ether (MTB ether), and the solution is washed by shaking twice with water and subsequently with 5% NaHCO3 solution. The organic phase is dried and evaporated. The residue is distilled in vacuo (2×10-2 mbar) (62° C. to 78°), to give ethyl 2-butylcyanoacetate.

Workup

  1. customwarms to about 55° C
  2. customis then hydrogenated at 30°
  3. custom(about 7 hours)
  4. customAfter the catalyst has been separated off
  5. customthe hydrogenation solution is evaporated on a rotary evaporator
  6. washmethyl tertiary-butyl ether (MTB ether), and the solution is washed
  7. stirringby shaking twice with water and subsequently with 5% NaHCO3 solution
  8. customThe organic phase is dried
  9. customevaporated
  10. distillationThe residue is distilled in vacuo (2×10-2 mbar) (62° C. to 78°)

Sources & evidence

ORD record
ord-d7f9d70ede2349108bf23d4689c3290a
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

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