Dimethyl Sulfoxide → 3-Methoxy-2-(pentyloxy)benzaldehyde

Temperature

0 °C

The crude product of (3-methoxy-2-pentyloxyphenyl)methanol (1.2 g), dimethyl sulfoxide (DMSO, 25 ml) and triethylamine (6.72 ml, 48.2 mmol) were mixed, and this solution was cooled to 0° C. Sulfur trioxide--pyridine complex (2.56 g, 16.1 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water to stop the reaction, and the aqueous layer was extracted 3 times with ethyl acetate (30 ml). The organic layers were combined, washed with 2N hydrochloric acid (30 ml), water (30 ml) and saturated brine (30 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=15/1-10/1) to give 3-methoxy-2-pentyloxybenzaldehyde (1.16 g, 83% in 3 steps) as a colorless oil.

1. additionSulfur trioxide--pyridine complex (2.56 g, 16.1 mmol) was added
2. customthe reaction
3. extractionthe aqueous layer was extracted 3 times with ethyl acetate (30 ml)
4. washwashed with 2N hydrochloric acid (30 ml), water (30 ml) and saturated brine (30 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe drying agent was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=15/1-10/1)

ORD record

ord-4619f26ca0ab42a5809218a8b39a7def

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919