Water → HCID 23116474, compound

Temperature

4 °C

2-[3,5-Bis(methoxymethoxy)-2-phenylphenyl]ethanol (1.2 g, 3.7 mmol) obtained in Example 3, Step 3 was dissolved in N,N-dimethylformamide (15 mL), and a 60% sodium hydride dispersion in mineral oil (0.30 g, 7.5 mmol) was added thereto in an atmosphere of nitrogen, followed by stirring at 4° C. for 4 minutes. After methyl iodide (0.70 mL, 11 mmol) was added dropwise to the reaction mixture, the mixture was stirred at 4° C. for 1 hour, followed by further stirring for 48 hours, while the temperature of the mixture was raised to room temperature. To the reaction mixture was added water (10 mL) and a saturated aqueous solution of ammonium chloride (20 mL), and the mixture was extracted with ethyl acetate (0.10 L). The organic layer was washed with water (0.10 L) and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2) to obtain 3,5-bis(methoxymethoxy)-1-(2-methoxyethyl)-2-phenylbenzene (1.1 g, 91%).

1. stirringthe mixture was stirred at 4° C. for 1 hour
2. stirringby further stirring for 48 hours, while the temperature of the mixture
3. temperaturewas raised to room temperature
4. extractiona saturated aqueous solution of ammonium chloride (20 mL), and the mixture was extracted with ethyl acetate (0.10 L)
5. washThe organic layer was washed with water (0.10 L)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationfollowed by concentration under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2)

ORD record

ord-3b78b0ce55894f33a5ad3d98298607b0

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538224B2