Water → 2-Chloro-4-fluoro-3-propylbenzaldehyde

2-Chloro-1-(dimethoxymethyl)-4-fluoro-3-propylbenzene (1.20 g) was dissolved in a mixed solvent of tetrahydrofuran (16 mL)-1 mol/L hydrochloric acid (8 ml), and the mixture was heated under reflux for 2 hr. To the reaction mixture were added water and ethyl acetate, and the mixture was extracted with ethyl acetate. The obtained extract was dried over anhydrous magnesium sulfate. The ethyl acetate solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=30:1→3:1) to give the title compound as a colorless oil (yield: 970 mg).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 2 hr
3. extractionthe mixture was extracted with ethyl acetate
4. extractionThe obtained extract
5. dry with materialwas dried over anhydrous magnesium sulfate
6. concentrationThe ethyl acetate solvent was concentrated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=30:1→3:1)

ORD record

ord-23d5bc4f10fc48e7b22c64b0a2e2564b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592452B2