Sodium Iodide → Ethyl 4-(3,4-dichlorophenoxy)butanoate

Participants

Reaction Steps

Potassium carbonate (27.5 mmol, 3.75 g) and sodium iodide (0.3333 mmol, 0.0500 g) were added to a reaction mixture of 3,4-dichloro-phenol Compound 16a (30.25 mmol, 4.93 g) and 4-bromo-butyric acid ethyl ester Compound 16b (27.5 mmol, 5.36 g) in acetone (60 mL). The reaction mixture was stirred overnight at room temperature. TLC analysis (4:1 hexane:EtOAc) showed no formation of product. The reaction mixture was refluxed for 3 hrs and TLC analysis (4:1 hexane:EtOAc) showed trace of starting material Compound 16a. The reaction mixture was refluxed overnight, then basified with 1N NaOH solution and extracted with CH2Cl2. The organics were dried over MgSO4. The drying agent was filtered and the solvent was removed in vacuo to yield 4-(3,4-dichloro-phenoxy)-butyric acid ethyl ester Compound 16c (6.9 g, 90.7%) as a pale pink oil, which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.21-1.31 (q, 3H), 2.12-2.25 (m, 2H), 2.45-2.53 (t, 2H), 3.95-4.02 (t, 2H), 4.10-4.20 (q, 2H), 6.71-6.78 (dd, 1H), 6.94-6.96 (d, 1H), 7.28-7.31 (d, 1H).

Provenance & Evidence