3-(4-CHLOROPHENOXY)PROPANENITRILE synthesis

Yield:46125-42-2 34%

Reaction Conditions:

with N,N,N-trimethylbenzenemethanaminium hydroxide in methanol; for 20 h;Reflux;

Steps:

3-(4-chlorophenoxy)propanenitrile

A two-neck flask was flushed with argon and charged with the reagents: 4-chlorophenol (5.12 g, 40.00 mmol, 1.0equiv), acrylonitrile (50 mL, 40.00 mmol, 1 equiv) and Triton B (40 wt% in methanol, 0.8 mL). The mixture was heatedto reflux for 20 h. After cooling to rt, 120 mL DCM was added. The mixture was washed with 2 × 75 mL 5% NaOH, 1 ×60 mL 2M HCl and 1 × 60 mL water. The organic phase was dried over MgSO4, filtered and evaporated to dryness. Thecrude product was purified by column chromatography (DCM:hexane 1:1). White crystals (2.44 g, 34%), mp 46.4-47.5°C. 1H NMR (CDCl3) δ (ppm): 7.29-7.23 (m, 2H), 6.87-6.81 (m, 2H), 4.16 (t, J = 6.4 Hz, 2H), 2.83 (t, J = 6.4 Hz, 2H).13C NMR (CDCl3) δ (ppm): 156.4, 129.7, 126.9, 117.1, 116.1, 63.0, 18.7.

References:

Carpéné, Christian;Viana, Pénélope;Iffiú-Soltesz, Zsuzsa;Tapolcsányi, Pál;F?ldi, Anna ágota;Mátyus, Péter;Dunkel, Petra [Molecules,2022,vol. 27,# 19,art. no. 6224] Location in patent:supporting information