Pyridine → Chloromethyl isopropyl carbonate

To a cold solution (approximately 10° C.) of chloromethylchloroformate (65 mL) in diethyl ether (1.4 L) was added isopropanol (56 mL) followed by a dropwise addition of pyridine (60 mL). After the addition the cold bath was removed and the reaction mixture was stirred for 18 h. The reaction mixture was poured into a separation funnel containing cold water (100 mL). The ether layer was separated and washed with water (100 mL×2) and then dried over Na2SO4. Evaporation of the solvent furnished the chloromethyl isopropyl carbonate (107 g, 95%). Chloromethyl isobutyl carbonate, chloromethyl neopentyl carbonate, chloromethyl tert butyl carbonate and chloromethyl 3-pentyl carbonate are prepared in a similar manner.

1. additionAfter the addition the cold bath
2. customwas removed
3. additionThe reaction mixture was poured into a separation funnel
4. additioncontaining cold water (100 mL)
5. customThe ether layer was separated
6. washwashed with water (100 mL×2)
7. dry with materialdried over Na2SO4
8. customEvaporation of the solvent

ORD record

ord-5a18e9dffecf4276a43febec24be3375

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE038333E1