Acetone → 2-(4-Fluorophenoxy)acetaldehyde

HRID 2397615Notes

Reaction equation

HRID 2397615 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.CC(C)=O.S(=O)(=O)(O)O>O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]=[O:3])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 114475181-(2,2-Diethoxyethoxy)-4-fluorobenzene

Product 1

HCID 110518692-(4-Fluorophenoxy)acetaldehydeYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-fluorophenoxyacetaldehyde diethyl acetal (30 g., 0.13 mole), acetone (150 ml.), water (150 ml.) and concentrated sulfuric acid (0.8 ml.) is stirred and heated at reflux for 16 hours. After cooling to 25° C., the reaction mixture is extracted with methylene chloride four times. The combined organic extract is washed with aqueous sodium bicarbonate, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo leaves a residual oil which is distilled to provide the title compound as a colorless oil (19 g., 94%) bp0.05 70° C.; pmr (CCl 4) δ 4.37 (2H, d), 6.6-7.1 (4H, m) and 9.68 (H, t).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. extractionthe reaction mixture is extracted with methylene chloride four times
  4. extractionThe combined organic extract
  5. washis washed with aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customEvaporation of the filtrate in vacuo
  9. customleaves a residual oil which
  10. distillationis distilled

Sources & evidence

ORD record
ord-796b6611b9784347bbcd8e77330eb6c8
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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