Propanal → (Z)-Methyl 3-methyl-4-oxobut-2-enoate

HRID 1590347Notes

Reaction equation

HRID 1590347 reaction equation
CO[CH:3](O)[C:4]([O:6][CH3:7])=[O:5].[CH:9](=[O:12])[CH2:10][CH3:11]>C(NCCCC)CCC>[CH:9](/[C:10](/[CH3:11])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])=[O:12]

Participants

4

Reactant 2

HCID 527PropanalHCID 2724791Methyl 2-Hydroxy-2-methoxyacetate

Product 1

HCID 12951418(Z)-Methyl 3-methyl-4-oxobut-2-enoateYield 52%

Reagents, catalysts & solvents 1

HCID 8148DibutylamineCatalyst

Procedure

3 g (0.025 mol) of di-n-butylamine were added at 20° C. to a stirred mixture of 120 g (1 mol) of methyl 2-methoxy-2-hydroxyacetate and 58 g (1 mol) of propionaldehyde. An exothermic reaction started immediately and the temperature of the reaction mixture rose to about 90° C., and it boiled vigorously. After about 10 min the temperature started to fall again and reached room temperature after about 1.5 h. Distillation of the reaction mixture yielded 66.4 g of methyl 3-formylcrotonate of b.p. 45°-58° C./8-9 mbar, corresponding to a yield of 52%. The trans/cis ratio was determined by gas chromatography to be 91/9.

Workup

  1. customAn exothermic reaction
  2. customrose to about 90° C.
  3. waitreached room temperature after about 1.5 h
  4. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-9530d6c72f0c4b339c46f3e7c5b5f902
Source dataset
uspto-grants-1993_04
Patent number
US05202461

Reaction notes

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