Potassium Carbonate → 4-fluoronaphthalen-1-ol

HRID 2075487Notes

Reaction equation

HRID 2075487 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([F:15])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([OH:4])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 23132789HCID 23132789, compound

Product 1

HCID 109208304-fluoronaphthalen-1-olYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2.71 g of 1-acetoxy-4-fluoro-naphthalene in 142 ml of degassed methanol was added a solution of 9.2 g of potassium carbonate in 95 ml of degassed water. The mixture was stirred at room temperature for 5 h. The mixture was cooled with ice, acidified to pH1-2 with conc. HCL, extracted with dichloromethane, dried (magnesium sulphate), filtered and concentrated to an orange solid. The material was purified by chromatography on silica gel eluting with dichloromethane/heptanes/toluene to provide 1.98 g of 4-fluoro-1-hydroxynaphthalene as a white solid.

Workup

  1. temperatureThe mixture was cooled with ice
  2. extractionextracted with dichloromethane
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated to an orange solid
  6. customThe material was purified by chromatography on silica gel eluting with dichloromethane/heptanes/toluene

Sources & evidence

ORD record
ord-a1dfb7593ab9405082e3c5ccaf4fcac1
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…