Hydrochloric Acid → 2,2-dimethyl-6-chloromethyl-1,3-dioxin-4-one

Temperature

-25 °C

A solution of 2,2,6-trimethyl-1,3-dioxin-4-one (16.0 g, 0.11 mol) in THF (50 ml) was added dropwise over 20 min to a solution of lithium diisopropylamide (75 ml, 2.0 M solution in heptane/THF/ethylbenzene, 0.15 mol) at the temperature of −78° C. During the addition, a fine yellow suspension formed. Subsequently, the enolate solution was stirred at −78° C. for another 1 h and then cannulated to a solution of hexachloroethane (39 g, 0.16 mol) in THF (200 ml) at −50° C. over 30 min. The resulting reaction mixture was then allowed to warm slowly to −25° C., and poured into ice-cold aqueous 10% hydrochloric acid (200 ml). The organic layer extracted with ether was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 15.9 g of yellow oil. The product was used without further purification. 1H NMR (CDCl3, ppm): δ 5.57 (s, 1H), 4.00 (s, 2H), 1.96 (s, 6H).

1. additionDuring the addition
2. customa fine yellow suspension formed
3. customThe resulting reaction mixture
4. extractionThe organic layer extracted with ether
5. washwas washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-bda1de6ee4a74ab38e275292afa3416e

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555027B2