Sodium Hydroxide → 1H-Perfluorooct-1-yne

HRID 1751153Notes

Reaction equation

HRID 1751153 reaction equation
[F:1][C:2]([F:25])([C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[C:3]#[C:4]C(C)(O)C.[OH-].[Na+]>>[F:1][C:2]([F:25])([C:9]([F:23])([F:24])[C:10]([F:21])([F:22])[C:11]([F:19])([F:20])[C:12]([F:17])([F:18])[C:13]([F:16])([F:15])[F:14])[C:3]#[CH:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 4353015,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-2-methyldec-3-yn-2-ol

Product 1

HCID 27763371H-Perfluorooct-1-yne

Conditions

Temperature
100 °C

Procedure

A flame-dried 50 mL round-bottom flask equipped with distillation apparatus was charged with 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-2-methyldec-3-yn-2-ol (S1) (35.3 g, 88 mmol) and NaOH pellets (2.5 g, 61 mmol) under argon. The pressure was reduced to 400 mmHg and the flask was heated to 100° C. The crude product was collected over an hour in a receiving flask in a brine/ice bath. The product was washed 3 times with distilled water and was subsequently dried over MgSO4. Removal of drying agent via filtration gave S2 (13.4 g, 46%) as a clear liquid. B.p. 92-94° C. 1H NMR (300 MHz, CDCl3): δ 3.07 (t, JH-F=5.7 Hz, 1H). 19F NMR (282 MHz, CDCl3): δ −126.69 (2F), −123.39 (2F), −123.25 (2F), −121.83 (2F), −99.76 (2F), −81.33 (3F).

Workup

  1. customA flame-dried 50 mL round-bottom flask equipped with distillation apparatus
  2. customThe crude product was collected over an hour in a receiving flask in a brine/ice bath
  3. washThe product was washed 3 times with distilled water
  4. dry with materialwas subsequently dried over MgSO4
  5. customRemoval
  6. customof drying agent
  7. filtrationvia filtration
  8. customgave S2 (13.4 g, 46%) as a clear liquid

Sources & evidence

ORD record
ord-73dbb4eea6994b82a4a47fb7f4723922
Source dataset
uspto-grants-2015_10
Patent number
US09156938B2

Reaction notes

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