Methyl iodide → 4,5-Dichloroguaiacol

Temperature

130 °C

A suspension of 4,5-dichlorocatechol (1 g, 5.62 mmol), potassium carbonate (780 mg, 5.62 mmol), and methyl iodide (0.34 mL, 5.62 mmol) in N,N-dimethylformamide (20 mL) was stirred rapidly at 130° C. for 20 hours, under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature before diluting with ethyl acetate (50 mL). The mixture was washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine solution (50 mL). The organic layer was separated and dried over sodium sulphate, and evaporated under reduced pressure to a deep brown solid. The crude material was purified by flash chromatography (eluting with 1:1 heptane/dichloromethane) to afford 4,5-dichloro-2-methoxyphenol as a white solid (490 mg, 45%).

1. temperatureto cool to room temperature
2. washThe mixture was washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine solution (50 mL)
3. customThe organic layer was separated
4. dry with materialdried over sodium sulphate
5. customevaporated under reduced pressure to a deep brown solid
6. customThe crude material was purified by flash chromatography (eluting with 1:1 heptane/dichloromethane)

ORD record

ord-eaee92278285480cb0c1e82ed6805c9a

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2