Hydrochloric Acid → 4-Methoxy-α-methyl-β-oxobenzenepropanal

10 g (60.9 mmol) of 4′-methoxypropiophenone was dissolved in 100 ml of methyl formate. At room temperature, sodium methoxide, 15.3 g (79.2 mmol) at a concentration of 28% in methanol solution was dropwise added to the solution over a period of 30 minutes, followed by stirring at the same temperature for 6 hours. To the reaction mixture was added 100 ml of water, and the solution pH was adjusted to 1 with concentrated hydrochloric acid, followed by stirring for further 1 hour. Thereafter, the reaction mixture was extracted with 100 ml of ethyl acetate three times. The organic phase was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. Filtration and subsequent distillation to remove the solvent gave 9.8 g (51.0 mmol) of 2-formyl-4′-methoxypropiophenone as a light yellow crystal. The yield was 84%. The product synthesized was subjected to the next reaction without purification.

1. stirringby stirring for further 1 hour
2. extractionThereafter, the reaction mixture was extracted with 100 ml of ethyl acetate three times
3. washThe organic phase was washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationFiltration and subsequent distillation
6. customto remove the solvent

ORD record

ord-4837ed8077ec4ebd991442348c9b5f75

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192906B2