Hydrochloric Acid → 3-Formyl-5-isopropyl-4-methoxybenzoic acid

To magnesium (2.43 g), tetrahydrofuran (100 mL), 5-bromo-1-diethoxymethyl-3-isopropyl-2-methoxybenzene (31.55 g) and a 0.97M methylmagnesium bromide-tetrahydrofuran solution (15 mL) were added, and then the mixture was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and stirred under a carbon dioxide atmosphere for 30 minutes, and then 2N hydrochloric acid (100 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The organic solvent was distilled off under reduced pressure, and then the mixture was extracted with diisopropylether. The organic layer was extracted with 1N sodium hydroxide (100 mL) added thereto, and then the aqueous layer was washed twice with diisopropylether. The aqueous layer was acidified with 4N hydrochloric acid added thereto, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (15.85 g) as a brown solid.

1. temperatureThe reaction solution was cooled to 0° C.
2. stirringstirred under a carbon dioxide atmosphere for 30 minutes
3. stirringthe reaction mixture was stirred at room temperature for 16 hours
4. distillationThe organic solvent was distilled off under reduced pressure
5. extractionthe mixture was extracted with diisopropylether
6. extractionThe organic layer was extracted with 1N sodium hydroxide (100 mL)
7. additionadded
8. washthe aqueous layer was washed twice with diisopropylether
9. additionadded
10. extractionextracted with ethyl acetate
11. washThe organic layer was washed with saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-4dd9d3d9430644e78ea72c690fbe1319

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367843B2