Isopropanol → 1,3-Dichloro-1,1,2,2,3-pentafluoropropane

HRID 1975808Notes

Reaction equation

HRID 1975808 reaction equation
[Cl:1][C:2](Cl)([F:10])[C:3]([F:9])([F:8])[C:4]([Cl:7])([F:6])[F:5].C(O)(C)C>>[Cl:7][C:4]([C:3]([CH:2]([F:10])[Cl:1])([F:9])[F:8])([F:6])[F:5]

Participants

3

Procedure

1,1,3-trichloro-1,2,2,3,3-pentafluoropropane(produced in Part C above) (106.6 g, 0.45 mol) and 300 g(5 mol) isopropanol were stirred under an inert atmosphere and irradiated 4.5 hours with a 450 W Hanovia Hg lamp at a distance of 2-3 inches(5-7.6 cm). The acidic reaction mixture was then poured into 1.5 liters ice water. The organic layer was separated, washed twice with 50 ml water, dried with calcium sulfate, and distilled to give 50.5 g ClCF2CF2CHClF, bp 54.5°-56° C. (55%). 1H NMR (CDCl3): ddd centered at 6.43 ppm. J H--C--F=47 Hz, J H--C--C--Fa=12 Hz, J H--C--C--Fb=2 Hz.

Workup

  1. customirradiated 4.5 hours with a 450 W Hanovia Hg lamp at a distance of 2-3 inches(5-7.6 cm)
  2. customThe organic layer was separated
  3. washwashed twice with 50 ml water
  4. dry with materialdried with calcium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-56e2ac0045884bf3a2623a6c8c2be509
Source dataset
uspto-grants-1994_02
Patent number
US05288819

Reaction notes

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