Benzene → 3-Chloro-2-methylbiphenyl

During a 45 minute period 3-chloro-2-methylaniline (141.6 g, 1.0 mole) was added to a stirred solution of isoamyl nitrite (175.6 g, 1.5 moles) in benzene (842 g, 10.0 moles). The reaction mixture was stirred at room temperature for two hours, heated at reflux for one hour, then cooled to room temperature. Approximately 2 l of n-heptane was added to the reaction mixture. Most of the solvents were distilled from the mixture under reduced pressure, followed by distillation at atmospheric pressure (until a head temperature of 95° was reached). The pot residue was dissolved in 2 l of n-heptane and the solution filtered through 250 g of silica gel. The filtrate was subjected to column chromatography on 250 g of silica gel, elution with n-heptane, to give an oil. The oil was rechromatographed on 250 g of silica gel, elution with n-heptane, to give an oil. The oil was distilled in a Kugelrohr distillation apparatus (90°/0.05 mm) to give 3-chloro-2-methyl-[1,1'-biphenyl] (23.5 g) as an oil.

1. temperatureheated
2. temperatureat reflux for one hour
3. temperaturecooled to room temperature
4. distillationMost of the solvents were distilled from the mixture under reduced pressure
5. distillationfollowed by distillation at atmospheric pressure (until a head temperature of 95°
6. dissolutionThe pot residue was dissolved in 2 l of n-heptane
7. filtrationthe solution filtered through 250 g of silica gel
8. washThe filtrate was subjected to column chromatography on 250 g of silica gel, elution with n-heptane
9. customto give an oil
10. customThe oil was rechromatographed on 250 g of silica gel, elution with n-heptane
11. customto give an oil
12. distillationThe oil was distilled in a Kugelrohr distillation apparatus (90°/0.05 mm)

ORD record

ord-55999275f7f5419db78c6c7465840385

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04536591