p-Toluenesulfonic acid → 1-Chloro-2-(methoxymethoxy)benzene

2-Chlorophenol (96.4 g, 0.75 mol), dimethoxymethane (257.9 g, 3.39 mol) and 750 mg of p-toluenesulfonic acid were dissolved in 1.5 L of methylene chloride and the mixture heated at reflux with stirring under nitrogen for 72 hours in a flask equipped with a Soxhlet extraction apparatus containing 400 g of 3A molecular sieves. The mixture was allowed to cool and 3 ml of triethylamine was added. The mixture was then extracted with 2N sodium hydroxide and the organic phase was dried over magnesium sulfate. Evaporation of the volatiles under reduced pressure left 66.9 g of crude 1-chloro-2-methoxymethoxybenzene as a residue. This was distilled and the fraction boiling at 94° C. and 6.5 mm pressure was collected to obtain 51.3 g (40 percent of theory) of purified product. The proton nmr spectrum was consistent with the assigned structure.

1. temperaturethe mixture heated
2. temperatureat reflux
3. customequipped with a Soxhlet extraction apparatus
4. temperatureto cool
5. extractionThe mixture was then extracted with 2N sodium hydroxide
6. dry with materialthe organic phase was dried over magnesium sulfate
7. customEvaporation of the volatiles under reduced pressure
8. waitleft 66.9 g of crude 1-chloro-2-methoxymethoxybenzene as a residue
9. distillationThis was distilled
10. customthe fraction boiling at 94° C. and 6.5 mm pressure was collected
11. customto obtain 51.3 g (40 percent of theory) of purified product

ORD record

ord-56372a4afebc4a3ab84dcdad4135b05a

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04979978