Water → HCID 131720186, compound

HRID 1377930Notes

Reaction equation

HRID 1377930 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23]Br.O>CN(C)C=O.C(OCC)C>[CH3:20][O:21][C:22]([O:25][CH3:26])([O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 71034-HydroxybiphenylHCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 131720186HCID 131720186, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Phenylphenol (1.70 g, 10 mmol) and cesium carbonate (3.91 g (12 mmol) were stirred at room temperature under a nitrogen atmosphere in 20 mL of dimethylformamide until it appeared that no more solid was dissolving. At that point, 1.42 mL (12 mmol) of bromoacetaldehyde dimethyl acetal (2.03 g, 12 mmol) were added to the mixture via syringe and the resulting brown suspension was stirred at room temperature overnight. The mixture was then heated under reflux for two hours and then stirred at room temperature overnight. At the end of this period, 100 mL of water and 200 mL of diethyl ether were added; the organics were extracted into the ether layer, which was separated, dried over anhydrous sodium sulfate and evaporated to yield 2.10 g (81% yield) of dimethoxy-2-(4-biphenyloxy)ethane.

Workup

  1. dissolutionwas dissolving
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for two hours
  4. stirringstirred at room temperature overnight
  5. extractionthe organics were extracted into the ether layer, which
  6. customwas separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-29a2fd03350946b3bf6246ef8e29f3cc
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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