Hydrochloric Acid → HCID 89690113, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzoate (119 g, 181 mmol) in N-methylpyrrolidone (476 mL), add potassium hydroxide (21.2 g, 378 mmol) and stir 25 min at 120° C. Allow the mixture to cool and then dilute with water (240 mL) and methyl-tert-butylether (100 mL). Adjust to pH=2.5 with 12 N hydrochloric acid. Separate the phases and wash the aqueous phase with methyl-tert-butylether (3×35 mL). Wash the combined organic extracts twice with water and once with brine. Concentrate the organic extracts in vacuo. Recrystallize the resultant residue from acetonitrile, filter, and dry to yield (78 g, 67%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.60-7.47 (m, 3H); 7.37-7.20 (m, 6H); 7.12-7.02 (m, 4H); 6.60 (s, 1 H); 5.00 (s, 2H); 4.20 (m, 4H); 3.00 (m, 2H); 2.61 (q, J=7.7 Hz, 2H); 2.33 (m, 2H); 1.59 (m, 2H); 1.18 (t, J=7.7 Hz, 3H); 0.98 (t, J=7.7 Hz, 3H).

Provenance & Evidence