3,5-Dichloroanisole

Chemical Properties

White to yellow crystalline powder

Uses

3,5-Dichloroanisole, is a chlorinated anisole derivative, possessing possible antibacterial activity. It is also an organic building block that can be used for the synthesis of chlorinated chemical compounds, such as polychlorinated dibenzofurans (PCDD/F).

General Description

3,5-Dichloroanisole on nitration under mild conditions yields 3,5-dichloro-2,4,6-trinitroanisole. The ³⁵Cl Nuclear Quadrupole Resonance (NQR) frequency and spin lattice relaxation time in 3,5-dichloroanisole has been measured.

Synthesis

Under the protection of nitrogen, 2L reaction flask was added 1,3,5-trichlorobenzene 254.1 g (1.4 mol), sodium methanol 151.2 g (2.8 mol, 30% methanol solution), heating to 65 ~ 75 , holding, tracking the reaction detection until the reaction is complete, filtration, 400 g of dichloromethane extraction, washed with water to neutral, drying, stripping off the solvent to get 3,5-dichloroanisole Crude product, plus spiked fractionation column for distillation, to get the main fraction 229.1 g, yield 93%, GC: 92%.

References

[1] Emsley, J., et al. “Conformations of 3,5-Dichloroanisole and 3,5-Dibromoacetophenone Determined from 1H Nuclear Magnetic Resonance Spectra of Nematic Solutions.” Journal of The Chemical Society-Perkin Transactions 1, 1995 1, 1976, pp. 805–07, https://doi.org/10.1039/P29760000805.