Methyl iodide → 1-(2-Methoxyethyl)-3,5-bis(methoxymethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

2-[3,5-Bis(methoxymethoxy)phenyl]ethanol (4.6 g, 19 mmol) obtained in Example 1, Step 2 was dissolved in N,N-dimethylformamide (40 mL), and a 60% sodium hydride dispersion in mineral oil (0.30 g, 7.5 mmol) was added thereto at 4° C. in an atmosphere of nitrogen, followed by stirring at 4° C. for 1 hour. Methyl iodide (3.6 mL, 58 mmol) was added dropwise to the reaction mixture, followed by stirring at 4° C. for 3 hours. To the reaction mixture were added a saturated aqueous solution of ammonium chloride (30 mL) and water (0.2 L), and the mixture was extracted with ethyl acetate (0.20 L). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2) to obtain a quantitative yield of 1,3-bis(methoxymethoxy)-5-(2-methoxyethyl)benzene. 1H-NMR (CDCl3, 270 MHz) δ (ppm): 6.61-6.59 (m, 3H), 5.14 (s, 4H), 3.59 (t, J=7.1 Hz, 2H), 3.48 (s, 6H), 3.36 (s, 3H), 2.83 (t, J=7.1 Hz, 2H)

Provenance & Evidence