Diglyme → HCID 23455911, compound

HRID 1702848Notes

Reaction equation

HRID 1702848 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].[F-:11].[K+].COCCOCCOC.Cl[C:23]([F:30])([F:29])[C:24]([Cl:28])=[C:25]([F:27])[F:26]>O>[F:11][C:3]([O:4][C:23]([F:30])([F:29])[C:24]([Cl:28])=[C:25]([F:27])[F:26])([C:5]([F:8])([F:7])[F:6])[C:2]([F:10])([F:9])[F:1]

Participants

6

Procedure

Hexafluoroacetone (16.6 g, 0.10 mol) was distilled into a stirred mixture of potassium fluoride (5.80 g, 0.10 mol) and 1-(2-methoxyethoxy)-2-methoxyethane (hereinafter referred to as diglyme) (100 ml) to give a homogeneous solution. This mixture was maintained at 25°-30° C. and treated with 1,2-dichloro-1,1,3,3-tetrafluoropropene (18.3 g, 0.10 mol, prepared according to J. E. Bissey, H. Goldwhite and D. G. Rowsell, J. Org. Chem., 32, 1542 (1967)). The mixture was stirred overnight and then it was poured into water (500 ml). The lower layer was washed with water (250 ml), dried, and distilled to give 1-(heptafluoro-2-propoxy)-1,1,3,3-tetrafluoro-2-chloropropene (13.0 g, 0.039 mol, 39%), bp 82°-83° C. whose structure was confirmed by the following: λmax 5.72 (CCl=CF2) and 7.5-10 μm (CF, C--O); 19F NMR, -64.9 (m) 2F, --OCF2C=C; -76.0 (2nd order m) 2F, C=CF2 ; -81.2 t J=5.7 Hz, each member d J=2.2 Hz) 6F, CF3 ; and -146.7 ppm (t J=22.9 Hz each member septet J=2.2 Hz) 1F, CFO.

Workup

  1. customto give a homogeneous solution
  2. temperatureThis mixture was maintained at 25°-30° C.
  3. washThe lower layer was washed with water (250 ml)
  4. customdried
  5. distillationdistilled

Sources & evidence

ORD record
ord-9cbba7e0d9e64b49bd9041a27a84262d
Source dataset
uspto-grants-1982_09
Patent number
US04349650

Reaction notes

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