Sodium Acetate → HCID 14675645, compound

HRID 2352303Notes

Reaction equation

HRID 2352303 reaction equation
I[CH:2]([CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].C([O-])(=O)C.[Na+]>[Pd].C(O)C>[F:19][C:14]([F:20])([C:15]([F:16])([F:17])[F:18])[CH2:13][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 14675644HCID 14675644, compound

Product 1

HCID 14675645HCID 14675645, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The reaction mixture containing 16.5 grams (0.04 mole) of the 10-iodo-12,12,13,13,13-pentafluorotridecanol of step (A), 2.0 grams of palladium/charcoal catalyst, and 3.3 grams (0.04 mole) of sodium acetate in 100 ml of ethanol was hydrogenated using a Parr hydrogenator. Upon completion of the uptake of the theoretical amount of hydrogen the reaction mixture was concentrated under reduced pressure and stirred with 125 ml of pentane. The mixture was filtered and the filtrate was concentrated under reduced pressure to a residual semi-solid. The residue was distilled under vacuum to yield 6.2 grams of 12,12,13,13,13-pentafluorotridecanol; b.p. 112° C./1.4 mm, which solidified on standing; m.p. 41°-43° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. concentrationUpon completion of the uptake of the theoretical amount of hydrogen the reaction mixture was concentrated under reduced pressure
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to a residual semi-solid
  4. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-5255e328c3084b73869f51b243d98c63
Source dataset
uspto-grants-1989_10
Patent number
US04876285

Reaction notes

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