(2,2-Dimethoxyethyl)(4-methoxyphenyl)sulfane → 2-((4-Methoxyphenyl)thio)acetaldehyde

1-[(2,2-Dimethoxyethyl)thio]-4-methoxybenzene (11.0 g) was dissolved in 1% aqueous hydrochloric acid (60 mL) and acetone (30 mL). The reaction mixture was refluxed for 2 h. Acetone was removed under reduced pressure and the residue was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with 20% ethyl acetate in hexanes to afford the desired product (8.5 g, 97%). 1H-NMR (400 MHz, CDCl3): 9.55 (t, J=4.2 Hz, 1H), 7.36 (m, 2H), 6.84 (m, 2H), 3.79 (s, 3H), 3.40 (d, J=4.2 Hz, 2H).

1. temperatureThe reaction mixture was refluxed for 2 h
2. customAcetone was removed under reduced pressure
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography on silica gel with 20% ethyl acetate in hexanes

ORD record

ord-1a1e406f2ab94cb9a404e8bc6b46e242

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767675B2