Sodium borohydride → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1388588Notes

Reaction equation

HRID 1388588 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9](=[O:14])[CH2:8][CH2:7]2>C(O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([OH:14])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 196994886-Fluoro-1,2,3,4-tetrahydronaphthalen-2-olYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (1.67 g) was added in portions to a solution of 6-fluoro-2-tetralone (6.56 g) in dry ethanol (30 ml) with stirring, keeping the temperature below 25° C. The mixture was then stirred at room temperature for 3 hours. The mixture was then diluted with a little ethyl acetate and concentrated to an oily residue. Dilute sulphuric acid was added dropwise until effervescence no longer occurred. The mixture was extracted with ether and the extract washed, dried, and concentrated to give an oil. This was distilled (b.p. 75-77/0.1 Torr) to give 6-fluorotetralin-2-ol (5.31 g) containing a trace of the tetralone starting material.

Workup

  1. customthe temperature below 25° C
  2. stirringThe mixture was then stirred at room temperature for 3 hours
  3. concentrationconcentrated to an oily residue
  4. additionDilute sulphuric acid was added dropwise until effervescence
  5. extractionThe mixture was extracted with ether
  6. washthe extract washed
  7. customdried
  8. concentrationconcentrated
  9. customto give an oil
  10. distillationThis was distilled (b.p. 75-77/0.1 Torr)

Sources & evidence

ORD record
ord-80fcd6266e90474a9d86e62215b9613f
Source dataset
uspto-grants-1984_02
Patent number
US04431834

Reaction notes

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