Cesium carbonate → HCID 90387289, compound

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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-bromo-2-(2-methoxyethoxy)ethane (9 mmol) was 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 provide pure 1-methoxy-4-[2-(2-methoxyethoxy)ethoxy]-2,5-di-tert-butyl-benzene in an 87% yield. 1H NMR (300 MHz, CDCl3): δ/ppm 6.83 (s, 1H), 6.82 (s, 1H), 4.14 (t, J=4.5 Hz, 2H), 3.89 (t, J=4.5 Hz, 2H), 3.80 (s, 3H), 3.72 (t, J=4.5 Hz, 2H), 3.58 (t, J=4.5 Hz, 2H), 3.40 (s, 3H), 1.38 (s, 9H)), and 1.35 (s, 9H). The purity was over 99.5% based GC-mass spectroscopy, and the molecular weight was observed at 338.3, which is consistent with the theoretical value, 338.5.

Provenance & Evidence