Oxalic Acid → 28419-86-5

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (40.5 g) in tetrahydrofuran (160 ml) at -10° C. was added a solution of n-butyllithium (1.66M in hexane solution, 241 ml) under nitrogen atmosphere. The mixture was stirred for 20 minutes and then 1-(N-tert-butyl)butylimine (50.9 g) was added at the same temperature. Stirring was continued for 20 minutes and then cooled to -65° C. A solution of isobutanal (28.8 g) in tetrahydrofuran (120 ml) was added to the solution. The reaction mixture was kept at -65° C. for 90 minutes, then warmed slowly to room temperature and stirred overnight. The resultant mixture was poured into a saturated aqueous oxalic acid solution (1.5 l) and the mixture was stirred for one hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (300 ml×2). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was distilled to give (E)-2-ethyl-4-methyl-2-pentenal (35.7 g) : bP 30°~55° C. at 1.0~10 mmHg.

Provenance & Evidence