p-Toluenesulfonic acid → HCID 23507821, compound

Participants

Reaction Steps

A solution of 4-(4-nitrophenyl)-4-oxobutyric acid (0.50 g, 2.2 mmol), 1-dodecanol (5.0 ml, 22 mmol), and p-toluenesulfonic acid (50 mg) in tetrahydrofuran (2.5 ml) was stirred 60 hours at room temperature then heated under reflux for 1.5 hours. Concentration of the reaction mixture in vacuo and purification by chromatography or silica gel (200 g) eluting with methylene chloride:hexane (1.1 to 2:1) followed by filtration of the solid product from a small volume of hexane gave, after drying under high vacuum, dodecyl 4-(4-nitrophenyl)-4-oxobytyrate (0.43 g) as a white solid. 1H NMR (DMSO-6, 300 MHz) δ: 0.86 (t, J=6.5 Hz, 3H, esterCH3), 1.07-1.35 (m, 18H, esterCH2's), 1.47-1.60 (m, 2H, esterCH2), 2.69 (t, J=6 Hz, 2H, CH2), 3.39 (t, J=6 Hz, 2H, CH2), 4.00 (t, J=6.5 Hz, 2H, esterCH2), 8.22 (d, J=9 Hz, 2H, Ar), 8.36 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C22H33NO5: C, 67.49; H, 8.50; N, 3.58. Found: C, 67.36; H, 8.54; N, 3.55.

Provenance & Evidence