Phenol → (2,2-Diethoxyethoxy)benzene

HRID 1942440Notes

Reaction equation

HRID 1942440 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([O:10][CH:11]([O:14][CH2:15][CH3:16])[CH2:12]Cl)[CH3:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[OH-].[Na+].CN(C)C=O>[CH2:8]([O:10][CH:11]([O:14][CH2:15][CH3:16])[CH2:12][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:9]

Participants

7

Reactant 4

HCID 996PhenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121282-Chloro-1,1-diethoxyethane

Product 1

HCID 96328(2,2-Diethoxyethoxy)benzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.94 g (10 mmol) of phenol, 1.52 g (10 mmol) of chloroacetaldehyde diethyl acetal, 2.77 g (20 mmol) of potassium carbonate, 500 mg of potassium iodide and 5 ml of dimethylformamide were heated for 1 hour at 175° C. under microwave conditions. The mixture was then diluted with 2M aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried with sodium sulfate and the solvent evaporated in vacuum. The crude product was obtained in almost quantitative yield.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-907d57b1e0434595b23a759968da1805
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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