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

HRID 1249500Notes

Reaction equation

HRID 1249500 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-methylbutan-2-one 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. The mixture is allowed to cool and filtered. The filtrate is evaporated down, the residue is taken up with dichloromethane, the solution is washed once with 5% strength sodium hydroxide solution and once with water, dried over sodium sulphate and evaporated down, and the residue is distilled. 29 g (72% of theory) of 3-(1,3-dioxolan-2-yl)-1-(4-fluorophenoxy)-3-methylbutan-2-one of boiling point 143° C. to 145° C./0.1 mbar are obtained. ##STR93##

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe filtrate is evaporated down
  6. washthe solution is washed once with 5% strength sodium hydroxide solution and once with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated down
  9. distillationthe residue is distilled

Sources & evidence

ORD record
ord-c979960cbbb3427fa514c1260ca36adc
Source dataset
uspto-grants-1986_12
Patent number
US04632932

Reaction notes

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