Potassium Carbonate → 2-Chloro-4-(1-propoxy)toluene

3-Chloro-4-methylphenol (2.00 g) was dissolved in N,N-dimethylformamide (10.0 ml), and potassium carbonate (2.91 g) and 1-propyl iodide (2.62 g) were added. The mixture was stirred at room temperature for 20 hr, and the reaction mixture was concentrated under reduced pressure. Water was added, and the mixture was extracted with AcOEt. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with hexane:ethyl acetate=5:1. The objective fraction was concentrated under reduced pressure to give 2-chloro-4-(1-propoxy)toluene (2.18 g) as a colorless oil.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionWater was added
3. extractionthe mixture was extracted with AcOEt
4. washThe organic layer was washed successively with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. washeluted with hexane
8. concentrationThe objective fraction was concentrated under reduced pressure

ORD record

ord-4b110a38d15946b6bba7c390328297cd

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060721B1