Cesium carbonate → HCID 90386879, compound

Participants

Reaction Steps

2,5-di-tert-butyl-4-methoxyphenol (9 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 ml). Cesium carbonate (13 mmol) and 1-bromoethyl methyl ether (9 mmol) were added to the solution. The reaction mixture was then stirred at room temperature overnight. After removal of the solvent, the residue was partitioned between dichloromethane (DCM) and aqueous NaHCO3 (0.1 M). The organic portion was separated and dried over Na2SO4 and then the solvent was removed under vacuum. The crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1) to afford pure 1-methoxy-4-(2-methoxyethoxy)-2,5-di-tert-butyl-benzene in an 85% yield. 1H NMR (300 MHz, CDCl3): δ/ppm 6.84 (s, 1H), 6.83 (s, 1H), 4.11 (t, J=4.5 Hz, 2H), 3.78 (m, 5H), 3.45 (s, 3H), 1.38 (s, 9H), and 1.35 (s, 9H).

Provenance & Evidence