Acetone → 2-(4-Fluorophenoxy)acetaldehyde

HRID 1730120Notes

Reaction equation

HRID 1730120 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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-fluorophenoxyacetaldehyde diethyl acetal (30.0 g., 0.131 mole), acetone (150 ml.), water (150 ml.), and concentrated sulfuric acid (0.8 ml.) is refluxed overnight (ca. 16 hr.). The mixture is allowed to cool to room temperature and is then extracted with methylenechloride four times. The combined extracts are washed with aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The solvent is stripped off on a rotary evaporator and the oil residue is subsequently distilled in vacuo at 70°/0.05 mm to give the title compound (19.0 g., 0.123 mole, 94%). ir (neat) 3.23, 3.50, 3.63, 5.71, 6.62, 7.00, 8.00, 8.24, 9.07, 9.38, 12.03, 12.51, 13.12μ; pmr (CCl4) δ 4.37 (2H, d, J=1Hz), 6.6-7.1 (4H, m), 9.68 (1H, t, J=1Hz).

Workup

  1. temperatureis refluxed overnight (ca. 16 hr.)
  2. extractionis then extracted with methylenechloride four times
  3. washThe combined extracts are washed with aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent is stripped off on a rotary evaporator
  6. distillationthe oil residue is subsequently distilled in vacuo at 70°/0.05 mm

Sources & evidence

ORD record
ord-ffe69187c55d4a2ab3c60e62d04282ca
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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