Dimethyl Sulfoxide → 3-Hexyl-4-methoxybenzaldehyde

A crude product of (3-hexyl-4methoxyphenyl)methanol, dimethyl sulfoxide (DMSO, 1.5 ml) and triethylamine (0.46 ml, 3.3 mmol) were mixed in a stream of argon. To this solution was added sulfur trioxide-pyridine complex (159 mg, 1 mmol) under ice-cooling, and the mire was stirred at room temperature for 1 hour. This reaction mixture was poured into water (20 ml) to stop the reaction. The aqueous layer was extracted 3 times with ethyl acetate (20 ml). The organic layer was washed successively with 2N hydrochloric acid (20 ml), water (20 ml) and saturated brine (30 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (hexane/ethyl acetate=1/1) to give 3-hexyl-4-methoxybenzaldehyde (75.4 mg, 92% in 2 steps) as a colorless oil.

1. additionTo this solution was added sulfur trioxide-pyridine complex (159 mg, 1 mmol) under ice-
2. temperaturecooling
3. customthe reaction
4. extractionThe aqueous layer was extracted 3 times with ethyl acetate (20 ml)
5. washThe organic layer was washed successively with 2N hydrochloric acid (20 ml), water (20 ml) and saturated brine (30 ml)
6. dry with materialThis solution was dried over anhydrous magnesium sulfate
7. filtrationthe drying agent was filtered off
8. concentrationThe filtrate was concentrated under reduced pressure
9. customthe obtained residue was purified by column chromatography (hexane/ethyl acetate=1/1)

ORD record

ord-b0544a0504404f33aa9b3c98b90237a2

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919