2-Phenylbutyric Acid → HCID 19102936, compound

Participants

Reaction Steps

A solution of dicyclohexylcarbodiimide (6.91 g, 0.033 mol) in 33 mL of dry dioxane was added to a solution of 2-phenylbutyric acid (5.00 g, 0.030 mol) and N-hydroxysuccinimide (3.86 g, 0.034 mol) and the resulting mixture was allowed to stir overnight. The precipitated dicyclohexylurea by-product was filtered off and the filtrate concentrated under vacuum. The residue was dissolved in 5 mL of methylene chloride and filtered to remove a small amount of additional urea by-product. The solution was evaporated to give a white solid which was recrystallized from methanol to give 5.17 g (65%) of the product as white crystals; mp 96.5°-97.5° C.; 1H NMR (CDCl3) δ 0.99 (t, 3 H, J=7.4 Hz), 1.85-2.00 (m, 1 H), 2.13-2.28 (m, 1 H), 2.72 (br s, 4 H), 3.78 (t, 1 H, J=7.6 Hz), 7.35 (s, 5 H); 13C NMR (CDCl3) δ 11.49, 25.30, 26.89, 50.25, 127.95, 128.18, 128.92, 136.90, 169.24, 169.62; Anal. Calcd for C14H15NO4 : C, 64.36; H, 5.79; N, 5.36. Found: C, 64.63; H, 5.84; N, 5.34.

Provenance & Evidence