Perfluoro(3-isopropyl-4-methyl-2-pentene) → HCID 23440025, compound

Temperature

-78 °C

Under argon atmosphere, 1.0 mmol (459 mg) of hexafluoropropene trimer mixture [including 5 wt % of perfluoro-(3-ethyl-2,4-dimethyl-2-pentene)] comprising perfluoro-(4-methyl-3-isopropyl-2-pentene) as a main component was put in a 100 ml egg-plant-shaped flask with a three-way stopcock having a magnet stirrer made of Teflon (R) therein. Then, 10 ml of anhydrous ether dry-distilled on sodium was added into the mixture, and stirringly dissolved therein. 0.5 ml (1.0 mmol) of cyclohexane-ether solution containing 17% of phenyl lithium was dropped into the mixture from a dropping funnel in the interval of about 3 minutes, while maintaining the mixture at about −78° C. by cooling the reaction vessel in a dry ice-ethanol bath. After continuously stirring at about −50° C. for about 3 hours, the resulting reacted mixture became a yellow solution including a brown solid. The reaction mixture was poured into 30 ml of ice water. Then, 20 ml of ether was added therein to extract a target compound, and the extracted compound was rinsed with 30 ml of salt solution. After the reacted ether mixture was dried with magnesium sulfate for one night, the resulting mixture was subjected to reduced-pressure distillation under a vacuum of 5 mmHg to remove ether, and then subjected to reduced-pressure distillation under a vacuum of 10 mmHg. As a result, a mixture of 3 different conformational isomers of 2-phenyl-perfluoro-(4-methyl-3-isopropyl-2-pentene) was obtained. The respective structures of the obtained compounds were determined by 19F-NMR, 1H-NMR, GC-MS and others. The yields of conformational isomers A, B and C of 2-phenyl-perfluoro-(4-methyl-3-isopropyl-2-pentene) calculated from the integral ratio of the peak areas of the 19F-NMR spectrum were about 24% , 16% and 12%, respectively.

1. customwas put in a 100 ml egg-plant-shaped flask with a three-way stopcock
2. distillationThen, 10 ml of anhydrous ether dry-distilled on sodium
3. additionwas added into the mixture
4. dissolutionstirringly dissolved
5. additionwas dropped into the mixture from a dropping funnel in the interval of about 3 minutes
6. temperatureby cooling the reaction vessel in a dry ice-ethanol bath
7. customthe resulting reacted mixture
8. extractionto extract a target compound
9. washthe extracted compound was rinsed with 30 ml of salt solution
10. dry with materialAfter the reacted ether mixture was dried with magnesium sulfate for one night
11. distillationthe resulting mixture was subjected to reduced-pressure distillation under a vacuum of 5 mmHg
12. customto remove ether
13. distillationsubjected to reduced-pressure distillation under a vacuum of 10 mmHg
14. additionAs a result, a mixture of 3 different conformational isomers of 2-phenyl-perfluoro-(4-methyl-3-isopropyl-2-pentene)
15. customwas obtained

ORD record

ord-e30831f99cca46dabfb6900353283b7d

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689923B2