Acetic Acid → HCID 86762526, compound

Participants

Reaction Conditions

Reaction Steps

A reaction flask was charged with sec-butylmagnesium chloride (2 M, 1.6 L) and cooled to −10° C. 3-Methyl-butyraldehyde (260 g) was fed over about 2 hours while the temperature was kept under 15° C. The reaction mixture was aged to room temperature over about 6 hours and then poured into a mixture of ice and acetic acid (216 g). Toluene (400 mL) was added and aqueous and organic layers were split. The organic layer was separated and washed sequentially with sodium carbonate, brine, and water. The resulting organic layer containing crude 2,5-dimethyl-heptan-4-ol, crotonic acid (129 g), toluene (150 mL), and PTSA (10 g) were then charged into to 3-L reaction flask fitted with a Bidwell-Sterling trap. The reaction mixture was heated to reflux. Water was collected and removed via the Bidwell-Sterling trap. The reaction mixture was aged at reflux for about 18-20 hours till GC analysis showed completion of the reaction. The resulting reaction mixture was washed sequentially with sodium carbonate (twice) and brine, rush-over distilled and further fractional distilled to provide but-2-enoic acid 1-isobutyl-2-methyl-butyl ester (143 g) with a boiling point of 100° C. at 0.72 mmHg.

Provenance & Evidence