Acetone → 2-(4-Fluorophenoxy)acetaldehyde

HRID 460839Notes

Reaction equation

HRID 460839 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 hours). 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 hours)
  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-50641f48493e4ba9a5b568f60b1c952e
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

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