Potassium Carbonate → 2-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde

Participants

Reaction Steps

A mixture of crude 2-chloro-5-hydroxy-4-methoxy-benzaldehyde (1.79 g, 8.15 mmol), 1-bromo-3-methoxypropane (1.53 g, 9.79 mmol) and anhydrous K2CO3 (1.69 g, 12.2 mmol) in MeCN (30 mL) is refluxed overnight. Ice water is added to the mixture, followed by extraction with AcOEt. The combined organics are washed with brine, dried (Na2SO4) and concentrated. The title compound is obtained after purification by RP-HPLC on a PrepC18 OBD column (dimensions: 30×100 mm; 5 μM particle size, SunFire Ltd), and using a 95-5% gradient of MeCN/H2O 5:95 (containing 0.1% TFA) to MeCN/H2O 95:5 (containing 0.1% TFA) over 20 min, as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.42. MS: 259.0 [M+H]+. ]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.15 min. 1H-NMR (CDCl3): δ 2.15 (m, 2H), 3.39 (s, 3H), 3.59 (m, 2H), 3.99 (s, 3H), 4.19 (m, 2H), 6.91 (s, 1H), 7.45 (s, 1H), 10.4 (s, 1H) ppm.

Provenance & Evidence