Propanal → 3,5,5-Trimethylhexanal

HRID 845371Notes

Reaction equation

HRID 845371 reaction equation
CO.[OH-].[Na+].[CH3:5][CH:6]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH:8]=[O:9].[CH:15](=[O:18])[CH2:16][CH3:17]>C(O)(=O)C>[CH3:5][CH:6]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH:8]=[O:9].[CH3:17][C:16](=[CH:8][CH2:7][CH:6]([CH3:5])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:15]=[O:18]

Participants

7

Reactant 4

HCID 527PropanalHCID 887MethanolHCID 14798Sodium HydroxideHCID 215743,5,5-Trimethylhexanal

Product 2

HCID 215743,5,5-TrimethylhexanalHCID 539973842,5,7,7-Tetramethyloct-2-enal

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

128 g (4 moles) of methanol and 2 g (0.05 mole) of NaOH were initially taken under nitrogen in a reaction flask and were refluxed. A mixture of 142 g (1 mole) of 3,5,5-trimethylhexanal and 116 g (2 moles) of propionaldehyde was added dropwise to this solution in the course of 10 minutes. The resulting reaction mixture was kept at the boil for 1 hour (h) and then brought to pH 4-5 with an 80% strength aqueous acetic acid solution. After washing twice with water, the organic phase was separated off and worked up by fractional distillation. 32 g of unconverted 3,5,5-trimethylhexanal, as light ends, and 113 g of 2,5,7,7-tetramethyl-2-octenal (bp.=108°-111° C./14 mbar) were obtained, corresponding to a selectivity of 81%, based on trimethylhexanal; nD25 =1.4580.

Workup

  1. temperaturewere refluxed
  2. additionwas added dropwise to this solution in the course of 10 minutes
  3. customThe resulting reaction mixture
  4. washAfter washing twice with water
  5. customthe organic phase was separated off
  6. distillationworked up by fractional distillation

Sources & evidence

ORD record
ord-2e74adac17c54f08951ed687b778ed36
Source dataset
uspto-grants-1988_07
Patent number
US04758548

Reaction notes

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