Potassium Hydroxide → HCID 57455069, compound

Temperature

97 °C

Referring to scheme (17A) above, to a three-neck 500 mL flask equipped with a agitator, an inlet for a starting material addition, and a packed column topped with a reflux distillation head, thermocouple, and collection flask can be charged 60.40 g of KOH (0.917 mole), 5.86 g of Methyltributylammonium chloride (Aliquat 175, ˜5% by wt) in 150 mL of deionized water to form a solution. The resulting solution can be heated 97° C. and 110 g (0.281 mole) 1,1,1,2,5,5,5-heptafluoro-2-(trifluoromethyl)-4-iodopentane can be added drop-wise and sub-surface via syringe pump over the course of 2 hr period. During this addition the resulting product can be collected in the overhead collection flask and the reaction can be continued to be heated until the overhead temperature reached 94° C. The collected material can be dried over magnesium sulfate to give 74.18 g of crude reaction product which by GC analysis consisted on primary product and starting material. The crude reaction material was distilled to afford 42.6 g of (E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene (57.5% isolated yield). (1H-NMR (CDCl3): □ 6.45 (d, J=12 Hz, 1H), 6.45 (dhep, 1H). 13C-NMR (CDCl3): 90.5 (dhep, J=27, 202 Hz, CFCH), 120 (qd, 27, 287 Hz, CF3CF), 121.6 (q, J=220 Hz, CHCF3), 124.4 (m, CHCF), 128.2 (qd, J=21, 36 Hz, CHCF3). 19F-NMR (CDCl3w/CCl3F): □ −66.4 (d, JH−F=3 HzCF3CH), −76.9 (d, JF−F=8 Hz, CF3CF), −186.9 (m, CF3CF).

1. customequipped with a agitator, an inlet for a starting material addition
2. distillationa packed column topped with a reflux distillation head
3. customthermocouple, and collection flask
4. customto form a solution
5. customover the course of 2 hr period
6. additionDuring this addition the resulting product
7. customcan be collected in the overhead collection flask
8. customthe reaction
9. temperatureto be heated until the overhead temperature
10. customreached 94° C
11. dry with materialThe collected material can be dried over magnesium sulfate
12. customto give 74.18 g of crude
13. customreaction product which by GC analysis
14. customThe crude reaction material
15. distillationwas distilled

ORD record

ord-4ee42a7562c74a84976c49e3243ecd22

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943567B2