Hydrochloric Acid → HCID 20513456, compound

HRID 1164039Notes

Reaction equation

HRID 1164039 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:3]=1N.Cl.N([O-])=[O:19].[Na+].F[B-](F)(F)F.[H+]>C(O)(=O)C.O>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[C:3]=1[OH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 28118Tetrafluoroboric acidHCID 20513508HCID 20513508, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20513456HCID 20513456, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-methyl-6-(2-fluorophenoxy)aniline (27 g) in a mixture of conc. hydrochloric acid (26 ml) and water (85 ml), aqueous solution (15 ml) of sodium nitrite (8.6 g) and 42% fluoroboric acid (27 ml) were treated in a similar manner to that of Example 5-(1). To the resultant diazonium salt was added glacial acetic acid (500 ml), and the mixture was refluxed under heating for 6 hours. After cooling, the reaction mixture was evaporated, and water was added to the residue. The mixture was extracted with n-hexane, and the extract was washed with water and saturated aqueous sodium bicarbonate, dried and evaporated. To the oily residue were added 20% aqueous sodium hydroxide and ethanol, and the mixture was refluxed under heating for an hour, and then evaporated. Water was added to the residue, washed with n-hexane, acidified with conc. hydrochloric acid and extracted with n-hexane. The extract was washed with water, dried and evaporated. The residue was subjected to column chromatography on silica gel (220 g) and eluted with benzene to give oily 6-(2-fluorophenoxy)-o-cresol (13.6 g).

Workup

  1. additionwere treated in a similar manner to that of Example 5-(1)
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 6 hours
  4. temperatureAfter cooling
  5. customthe reaction mixture was evaporated
  6. additionwater was added to the residue
  7. extractionThe mixture was extracted with n-hexane
  8. washthe extract was washed with water and saturated aqueous sodium bicarbonate
  9. customdried
  10. customevaporated
  11. additionTo the oily residue were added 20% aqueous sodium hydroxide and ethanol
  12. temperaturethe mixture was refluxed
  13. temperatureunder heating for an hour
  14. customevaporated
  15. additionWater was added to the residue
  16. washwashed with n-hexane
  17. extractionextracted with n-hexane
  18. washThe extract was washed with water
  19. customdried
  20. customevaporated
  21. washeluted with benzene

Sources & evidence

ORD record
ord-d86fa39cd7294de38fbbfe90dfedb261
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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