Potassium Iodide → 4-Phenoxyphenoxyacetaldehyde diethyl acetal

HRID 35276

Reaction equation

HRID 35276 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:23]([O:25][CH:26]([O:29][CH2:30][CH3:31])[CH2:27]Br)[CH3:24]>CN(C)C=O>[CH2:23]([O:25][CH:26]([O:29][CH2:30][CH3:31])[CH2:27][O:22][C:19]1[CH:18]=[CH:17][C:16]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:21][CH:20]=1)[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 137717034-Phenoxyphenoxyacetaldehyde diethyl acetal

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

150 g of potassium carbonate and 4 g of finely powdered potassium iodide are added to a solution of 112 g (0.6 mole) of 4-phenoxyphenol and 157.6 g (0.8 mole) of bromoacetaldehyde diethyl acetal in 480 ml of dimethylformamide, and the batch is heated, under nitrogen, for 14 hours at 150° C. The salts are then removed by filtration from the reaction solution, and most of the dimethylformamide is distilled off in a water jet vacuum. The residue is dissolved in ether and the resultant solution is washed twice with water, three times with 20% potassium hydroxide solution and again with water. The ethereal solution is then dried over sodium sulfate and the ether is distilled off entirely. The resultant 4-phenoxyphenoxyacetaldehyde diethyl acetal is used without further purification for the preparation of the free aldehyde.

Workup

  1. customThe salts are then removed by filtration from the reaction solution
  2. distillationmost of the dimethylformamide is distilled off in a water jet vacuum
  3. dissolutionThe residue is dissolved in ether
  4. washthe resultant solution is washed twice with water, three times with 20% potassium hydroxide solution and again with water
  5. dry with materialThe ethereal solution is then dried over sodium sulfate
  6. distillationthe ether is distilled off entirely
  7. customThe resultant 4-phenoxyphenoxyacetaldehyde diethyl acetal is used without further purification for the preparation of the free aldehyde

Sources & evidence

ORD record
ord-4d3ab34c7ec543f8a4e739c64817eae9
Source dataset
uspto-grants-1988_08
Patent number
US04766152

Linked notes

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