Potassium Hydroxide → HCID 10203522, compound

Participants

Reaction Steps

To a solution of 7-oxo-2,12-dimethyl-2,12-diphenyl-tridecanedioic acid diethyl ester (3.93 g, 7.55 mmol) in ethanol (60 mL) was added a solution of KOH (4.0 g, 85%, mmol) in water (10 mL). The reaction mixture was heated under reflux for 3 h and then kept overnight at rt. The solution was concentrated under reduced pressure. The residue was dissolved in water (100 mL) and washed with ether (2×75 mL). The aqueous layer was acidified with concd. HCl (ca. 12 mL) until pH 1. The product was extracted with diethyl ether (3×75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to give 7-oxo-2,12-dimethyl-2,12-diphenyl-tridecanedioic acid as an oil (3.0 g, 90%). 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.40-7.10 (m, 10H), 2.32 (t, J=7.2 Hz, 4H), 2.10-1.80 (m, 4H), 1.6-1.45 (m, 10H), 1.25-1.10 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.1, 182.5, 142.8, 128.4, 126.9, 126.0, 49.9, 42.3, 38.7, 24.2, 24.0, 22.3. HRMS (LSIMS, nba): Calcd. for C27H35O5 (MH+): 439.2484, found 439.2497.

Provenance & Evidence