Hydrochloric Acid → Methyl 5-oxohexanoate

Participants

Reaction Steps

Calix[4]pyrrole meso-monoester 3. 4-Acetylbutyric acid (3.8 g, 29 mmol) was dissolved in methanol (50 mL) in a 100 mL round bottomed flask with magnetic stirring. Concentrated hydrochloric acid (1 mL, 37%) was added and the mixture heated at reflux for 12 hr. The solvent was then removed in vacuo and the residue redissolved in dichloromethane (50 mL). The solution was then washed with saturated NaHCO3 (aq) solution (2×50 mL) and then brine (1×100 mL). The organic layer was separated and then dried over MgSO4 and reduced in vacuo to give the methyl ester, methyl-4-acetylbutyrate, as a yellow oil (3.5 g, 24.3 mmol) corresponding to a yield of 84%. 1H NMR (CDCl3) 3.64 (s, 3, OCH3), 2.49 (t, J=7.2 Hz, 2, CH2), 2.32 (t, J =7.2 Hz, 2, CH2), 2.12 (s, 3, CH3), 1.86 (m, 2, CH2). 13C NMR (CDCl3) 207.0, 172.8, 50.7, 41.7, 32.3, 29.1, 18.25. CI MS m/z @ 145 (MH+)

Provenance & Evidence