4-Fluorophenol → 3-(1,3-Dioxolan-2-yl)-1-(4-fluorophenoxy)-3-methylbutan-2-one

HRID 980845Notes

Reaction equation

HRID 980845 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11](=[O:20])[C:12]([CH:15]1[O:19][CH2:18][CH2:17][O:16]1)([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:12]([CH3:14])([CH3:13])[C:11](=[O:20])[CH2:10][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 132699801-Chloro-3-(1,3-dioxolan-2-yl)-3-methylbutan-2-one

Product 1

HCID 132699843-(1,3-Dioxolan-2-yl)-1-(4-fluorophenoxy)-3-methylbutan-2-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 16.7 g (0.15 mol) of 4-fluorophenol, 29 g (0.15 mol) of 1-chloro-3-(1,3-dioxolan-2-yl)-3-methyl-2-butanone and 23.4 g (0.17 mol) of powdered potassium carbonate in 300 ml of methyl ethyl ketone is heated under reflux for 16 hours. It is allowed to cool and is filtered. The filtrate is concentrated, the residue is taken up in dichloromethane, the mixture is washed once with 5% strength sodium hydroxide solution and once with water, dried over sodium sulphate and concentrated and the residue is distilled. 29 g (72% of theory) of 3-(1,3-dioxolan-2-yl)-1-(4-fluorophenoxy)-3-methyl-2-butanone of boiling point 143° C. to 145° C./0.1 mbar are obtained. ##STR97##

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. temperatureto cool
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. washthe mixture is washed once with 5% strength sodium hydroxide solution and once with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-266bb5d62f9844398de818ec32a5e619
Source dataset
uspto-grants-1987_01
Patent number
US04639462

Reaction notes

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