Methane, dichloromethoxy- → 2-Methoxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde

4-(4-methoxyphenoxy)-5-methyl-7-nitroindane (5.0 g) and dichloromethyl methyl ether (3.02 mL) were dissolved in dichloromethane (50 mL). To the solution was added dropwise titanium tetrachloride (3.67 mL) under ice-cooling with stirring. The reaction mixture was stirred at room temperature under an argon atmosphere for 20 hours. After adding ice water (300 mL), the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was triturated with hexane (50 mL) and diethyl ether (5 mL), and the insoluble material was collected by filtration and washed with hexane to give the title compound (4.37 g).

1. temperaturecooling
2. stirringThe reaction mixture was stirred at room temperature under an argon atmosphere for 20 hours
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed under reduced pressure
7. customThe residue was triturated with hexane (50 mL) and diethyl ether (5 mL)
8. filtrationthe insoluble material was collected by filtration
9. washwashed with hexane

ORD record

ord-e1ac0c6ed2244fd2afa6481a2c629b3e

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230031B2