tert-Butanol → Heptafluoro-2-naphthol

HRID 279688Notes

Reaction equation

HRID 279688 reaction equation
[F:1][C:2]1[C:3]([F:18])=[C:4]([F:17])[C:5]([F:16])=[C:6]2[C:11]=1[C:10]([F:12])=[C:9](F)[C:8]([F:14])=[C:7]2[F:15].[OH-].[K+].C([OH:25])(C)(C)C>O>[F:1][C:2]1[C:3]([F:18])=[C:4]([F:17])[C:5]([F:16])=[C:6]2[C:11]=1[C:10]([F:12])=[C:9]([OH:25])[C:8]([F:14])=[C:7]2[F:15]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 67564Perfluoronaphthalene

Product 1

HCID 2724940Heptafluoro-2-naphtholYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

For about 3.5 hours, a mixture of 25 g octafluoronaphthalene (PCR Inc.; Gainesville, Fla.), 12 g KOH, and 100 mL tertiary butyl alcohol was refluxed. Water was added, and the tertiary butyl alcohol was distilled from the reaction mixture. The residue remaining in the flask was acidified with HCl and the aqueous mixture was extracted three times with 75 mL dichloromethane. The combined extracts were washed twice with 150 mL distilled water, dried over MgSO4, and rotary evaporated to yield a semi-crystalline solid. Recrystallization from hot hexanes gave 18 g heptafluoro-2-naphthol (72% yield) as slightly tan colored crystals.

Workup

  1. temperaturewas refluxed
  2. distillationthe tertiary butyl alcohol was distilled from the reaction mixture
  3. extractionthe aqueous mixture was extracted three times with 75 mL dichloromethane
  4. washThe combined extracts were washed twice with 150 mL
  5. distillationdistilled water
  6. dry with materialdried over MgSO4
  7. customrotary evaporated
  8. customto yield a semi-crystalline solid
  9. customRecrystallization from hot hexanes

Sources & evidence

ORD record
ord-45e8ddbe255145678a2f50c90b2073e5
Source dataset
uspto-grants-2002_03
Patent number
US06362379B1

Reaction notes

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