Glycol monoethyl ether acetate → Pentachlorophenyl perfluoroethoxymethyl ketone

Temperature

-40 °C

Hexachlorobenzene (35 g) was slurried in 160 ml of anhydrous ethyl ether at −40° C. A 2.5 M hexanes solution of n-butyllithium (54.1 mL) was added, and the reaction was stirred for 30 minutes at −40° C. Perfluoro-2-ethoxyacetylfluoride (40 g, 72 % pure, prepared from 2-ethoxyethyl acetate by the method described in Example 1 of U.S. Pat. No. 5,326,919, incorporated herein by reference) was added to the −40° C. reaction mixture which was then allowed to warm slowly to room temperature. The reaction mixture was quenched with 200 mL of cold 5% aqueous HCl. The aqueous mixture was extracted with ethyl ether and the extracts were dried over MgSO4 and rotary evaporated to give pentachlorophenyl perfluoroethoxymethyl ketone (49% crude yield). Vacuum distillation (105-109° C., 240 Pa) using a 15 cm Vigreux column gave 19.7 g of a colorless liquid which slowly crystallized on standing.

1. addition5,326,919, incorporated herein by reference) was added to the −40° C. reaction mixture which
2. temperatureto warm slowly to room temperature
3. customThe reaction mixture was quenched with 200 mL of cold 5% aqueous HCl
4. extractionThe aqueous mixture was extracted with ethyl ether
5. dry with materialthe extracts were dried over MgSO4
6. customrotary evaporated

ORD record

ord-c75356f87aac4623a8f943df076132d6

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313245B1