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

Temperature

4 °C

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.

1. customat 4° C.
2. stirringby stirring at 4° C. for 3 hours
3. extractionthe mixture was extracted with ethyl acetate (0.20 L)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2)

ORD record

ord-c706dd869ba7443abf3a646722db014f

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767693B2