Sulfuric Acid → HCID 20561441, compound

Temperature

-70 °C

In a 3 liter three neck round bottom flask fitted with a mechanical stirrer, dropping funnel equipped with a drying tube, and low temperature thermometer was placed a solution of 50.0 g. (0.158 mol) of dimethyl perfluoroadipate in 450 ml. of dry tetrahydrofuran (THF). The reaction mixture was cooled to -70° C. (dry ice-acetone) and 67.5 ml. (0.238 mol.) of Vitride (70% in benzene) diluted with 50 ml. of THF was added dropwise over 30 min. with vigorous stirring. The temperature of the reaction was maintained at ≤-70° C. during the addition and at -70° C. for 2.5 hours after addition was complete. To the viscous mixture 500 ml. of 20% sulfuric acid previously chilled at 5° C. was added dropwise. The temperature of the reaction was allowed to rise to -50° C. and maintained until the excess Vitride had been decomposed. The mixture was then allowed to warm spontaneously to room temperature. Ether (400-600 ml.) was added with vigorous stirring until a homogeneous two-phase system was obtained. The layers were separated and the aqueous phase extracted with an additional 200-300 ml. of ether. The combined ether extracts were washed to neutrality with brine, dried over MgSO4, and evaporated under reduced pressure. The title compound was left as a thick syrup, 45.2 g. (96% by weight), νmaxneat 3600-2000 (bd) cm-1.

1. customequipped with a drying tube
2. additionafter addition
3. additionwas added dropwise
4. customto rise to -50° C.
5. temperatureto warm spontaneously to room temperature
6. customwas obtained
7. customThe layers were separated
8. extractionthe aqueous phase extracted with an additional 200-300 ml
9. washThe combined ether extracts were washed
10. dry with materialdried over MgSO4
11. customevaporated under reduced pressure
12. waitThe title compound was left as a thick syrup, 45.2 g

ORD record

ord-0967c5262b024c9a9ec16d388c72caee

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04302612