Toluene → 4-Methoxy-4′-propylbiphenyl

Temperature

60 °C

In a nitrogen atmosphere, 20.00 g of 4-propylbromobenzene, 0.58 g of tetrakis-triphenylphosphine palladium, and 55 mL of an aqueous potassium carbonate solution (2 mol/L) were dissolved in 100 mL of ethanol, and the resultant solution was heated to 60° C. Then, a solution prepared by suspending 15.27 g of 4-methoxyphenylboronic acid in 60 mL of ethanol was added dropwise to the solution. After stirring at 60° C. for 2 hours, the mixture was allowed to cool to room temperature, and toluene was added to separate the mixture into layers. An aqueous layer was subjected to extraction with toluene, and the toluene extract was combined with an organic layer. The resultant mixture was washed with saturated brine and dried by adding sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized from ethanol to yield 21.60 g of 4-(4-propylphenyl)anisole.

1. customThen, a solution prepared
2. additionwas added dropwise to the solution
3. temperatureto cool to room temperature
4. customto separate the mixture into layers
5. extractionAn aqueous layer was subjected to extraction with toluene
6. extractionthe toluene extract
7. washThe resultant mixture was washed with saturated brine
8. customdried
9. additionby adding sodium sulfate
10. distillationthe solvent was distilled off under reduced pressure
11. customThe residue was purified by silica gel column chromatography
12. customrecrystallized from ethanol

ORD record

ord-704db088ea4841869cfb1f6451952571

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916718B2