Methane, dichloromethoxy- → HCID 20208798, compound

The product from step (a) (24.7 g, 0.1 mole) was dissolved in dry dichloromethane (500 ml) and the solution cooled to -15°. A solution of titanium tetrachloride (57.0 g, 21.6 ml, 0.3 mole) in dry dichloromethane (200 ml) was added dropwise with stirring and cooling. To the yellow-orange solution was added -dichloromethyl methyl ether (27.9 g, 22.0 ml, 0.24 mole) in dry dichloromethane (200 ml). The solution was stirred at -15° for 0.5 hr and warmed to room temperature over a period of 2 hr. The reaction mixture was poured onto ice/2N hydrochloric acid (21/500 ml) and stirred vigorously. The dichloromethane layer was separated and the aqueous layer extracted with dichloromethane (2×200 ml). The combined organic extracts were washed with water, dried (Na2SO4) and evaporated. The crude product was recrystallised from 50% aqueous methanol to give an off-white solid (24.0 g) mp 105°-6°.

1. temperaturethe solution cooled to -15°
2. temperaturecooling
3. stirringThe solution was stirred at -15° for 0.5 hr
4. additionThe reaction mixture was poured onto ice/2N hydrochloric acid (21/500 ml)
5. stirringstirred vigorously
6. customThe dichloromethane layer was separated
7. extractionthe aqueous layer extracted with dichloromethane (2×200 ml)
8. washThe combined organic extracts were washed with water
9. dry with materialdried (Na2SO4)
10. customevaporated
11. customThe crude product was recrystallised from 50% aqueous methanol

ORD record

ord-82f33dfe55bf41f4bbda77ab9f77ea5d

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04657929