Tetrafluoroethylene → HCID 13628172, compound

HRID 1981979Notes

Reaction equation

HRID 1981979 reaction equation
[F:1][C:2]([C:17]([F:20])([F:19])[F:18])([O:7][C:8]([F:16])([F:15])[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[C:3]([O:5][CH3:6])=[O:4].[F-:21].[K+].[I:23]Cl.[F:25][C:26]([F:30])=[C:27]([F:29])[F:28].OS([O-])=O.[Na+]>COCCOCCOCCOCCOC>[F:1][C:2]([C:17]([F:18])([F:19])[F:20])([O:7][C:8]([F:15])([F:16])[C:9]([F:21])([C:10]([F:13])([F:12])[F:11])[O:14][C:27]([F:29])([F:28])[C:26]([F:30])([F:25])[I:23])[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 5

HCID 8301TetrafluoroethyleneHCID 24640Iodine chlorideHCID 522689Potassium Fluoride2×HCID 15001768HCID 15001768, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13628172HCID 13628172, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8925TetraglymeSolvent

Procedure

Methyl perfluoro(5-keto-2-methyl-3-oxahexanoate) (54.4 g, 0.17 mol) was added to a suspension of 17.5 g (0.30 mol) of flame-dried KF in 160 ml of tetraglyme stirred at 10° to 15°. After the mixture had stirred until much of the KF dissolved, 54.9 g (0.34 mol) of iodine monochloride was added with cooling to maintain 20°. The resulting mixture was charged into a dry 400-ml metal tube and shaken while tetrafluoroethylene (36 g, 0.36 mol) was added under pressure. When no further pressure drop occurred, gases were vented. The reaction mixture was poured into ice water and decolorized by the addition of NaHSO3. The aqueous layer was extracted with CF2ClCFCl2, and the combined organic layers were dried over P2O5 and distilled to give 60.0 g (63%) of methyl perfluoro(8-iodo-2,5-dimethyl-3,6-dioxaoctanoate), bp 81° to 83° (16 mm), pure by GC. IR (neat): 2965 (sat'd CH), 1790 (C=O), 1250-1100 cm-1 (CF,C--O). NMR (CCl4): 'H 4.03 ppm (s, OCH3); 19F -64.7 (t,JFF 5.8 Hz, 2F, CF2I), -80.5 (m, 3F, CF3), -83.0 (d, JFF 2.5 Hz, 3F, CF3), -83.7 (m, 2F, CF2O), -132.2 (t of d of m, JFF 16.6, 2.5 Hz, 1F, CF), and -145.9 ppm (t of m, JFF 22 Hz 1F, CF), with AB branches for CF2O at -7375 and -7518 Hz (M,1F) and -8020 and -8162 Hz (d of m, JFF 22 Hz, 1F).

Workup

  1. dissolutiondissolved
  2. temperaturewith cooling
  3. temperatureto maintain 20°
  4. additionThe resulting mixture was charged into a dry 400-ml metal tube
  5. additionwas added under pressure
  6. extractionThe aqueous layer was extracted with CF2ClCFCl2
  7. dry with materialthe combined organic layers were dried over P2O5
  8. distillationdistilled

Sources & evidence

ORD record
ord-5f2506374eea4fa1b3af0ab71cc3a850
Source dataset
uspto-grants-1986_06
Patent number
US04594458

Reaction notes

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