Hydrochloric Acid → 2-Chloromethyl-5-dimethylaminomethyl-3-methylfuran

To a solution of 2-dimethylaminomethyl-3-methylfuran (6.5 g; 37.0 mmoles) [prepared in Step A] in 250 ml of chloroform was added paraformaldehyde (1.67 g; 55.7 mmoles) and zinc chloride (312 mg), and a slow stream of HCl gas was bubbled through while stirring at ambient temperature for 15 minutes. Stirring was continued for 2 hours, then HCl gas was bubbled through for 15 minutes and the mixture stirred for 1 hour. At this time additional paraformaldehyde (1.67 g; 55.7 mmoles) was added to the reaction mixture and a slow stream of HCl gas was passed through for 15 minutes. After stirring at ambient temperature for 18 hours, the reaction mixture was filtered through Celite and the filtrate evaporated under reduced pressure to yield the title compound (4.97 g) which crystallized upon standing and was used without further purification in Step C.

1. customa slow stream of HCl gas was bubbled through
2. stirringStirring
3. waitwas continued for 2 hours
4. customHCl gas was bubbled through for 15 minutes
5. stirringthe mixture stirred for 1 hour
6. customwas passed through for 15 minutes
7. stirringAfter stirring at ambient temperature for 18 hours
8. filtrationthe reaction mixture was filtered through Celite
9. customthe filtrate evaporated under reduced pressure

ORD record

ord-aa428244bd194bae8803f19ccd2a3c3d

Source dataset

uspto-grants-1985_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04510309