Hydrochloric Acid → 2-Cyclopropyl-6-fluorophenol

HRID 1866828Notes

Reaction equation

HRID 1866828 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH:18]1[CH2:20][CH2:19]1)(=O)C.Cl>CO>[CH:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=2[OH:10])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69046355HCID 69046355, compound

Product 1

HCID 229399142-Cyclopropyl-6-fluorophenolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (911 mg, 6.60 mmol) was added to a solution of 2-cyclopropyl-6-fluorophenyl acetate (640 mg, 3.30 mmol) in methanol (4 ml), and the mixture was stirred at room temperature for 1 hour. After 1M hydrochloric acid was added to the reaction mixture to adjust pH to 2, this was extracted with acetic acid. The organic layer was combined and washed with a saturated aqueous NaCl solution, followed by drying with anhydrous sodium sulfate. After the solid was removed by filtration, the filtrate was concentrated to obtain 497 mg of 2-cyclopropyl-6-fluorophenol.

Workup

  1. extractionthis was extracted with acetic acid
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialby drying with anhydrous sodium sulfate
  4. customAfter the solid was removed by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d3ae4b87efa84faf837aef6bb5053085
Source dataset
uspto-grants-2009_12
Patent number
US07629494B2

Reaction notes

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