4-Fluorophenol → HCID 20517757, compound

HRID 2198895Notes

Reaction equation

HRID 2198895 reaction equation
[CH3:1][C:2]([CH3:8])([C:4](=[O:7])[CH2:5]Cl)[CH3:3].[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]([CH3:8])([C:4](=[O:7])[CH2:5][O:16][C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)[CH3:3]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

Product 1

HCID 20517757HCID 20517757, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

418.3 g (3.11 mols) of 2,2-dimethyl-4-chloro-butan-3-one were added dropwise to a suspension, heated to the boiling point, of 315 g (2.8 mols) of 4-fluorophenol and 386.4 g (2.8 mols) of potassium carbonate in 1,500 ml of acetone. The mixture was stirred under reflux for 4 hours. After cooling to room temperature, the salt which had separated out was filtered off and the filtrate was concentrated in vacuo. The oil which remained was distilled in vacuo. 101.5 g (86.2% of theory) of 2,2-dimethyl-4-(4-fluorophenoxy)-butan-3-one of boiling point 83°-84° C./0.05 mm Hg (nD20 =1.4919) were obtained. ##STR49##

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe salt which had separated out
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. distillationThe oil which remained was distilled in vacuo

Sources & evidence

ORD record
ord-1b5634a4dd604010add6d6e2139012d4
Source dataset
uspto-grants-1982_11
Patent number
US04360528

Reaction notes

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