Diethyl Ether → 2,2-Bis(2-hydroxyphenyl)propane

HRID 1460386Notes

Reaction equation

HRID 1460386 reaction equation
[H-].[Na+].C[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20]C)([CH3:13])[CH3:12].CCOCC>CN(C)C=O>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 5787142,2-Bis(2'-methoxyphenyl)propane

Product 1

HCID 5771572,2-Bis(2-hydroxyphenyl)propaneYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 l flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure.

Workup

  1. extractionextracted twice with pentane
  2. additionTo this was added first 250 ml of dimethylformamide
  3. temperaturethe mixture was heated
  4. temperatureat reflux
  5. stirringwith stirring for 24 hours
  6. waitto stand at ambient temperature for another approximately 18 hours
  7. extractionthe resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution
  8. additionEther (500 ml) was then added
  9. stirringafter shaking
  10. customthe ether layer was separated
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-915ff0f6f970476dbcfaa9846f595129
Source dataset
uspto-grants-1991_12
Patent number
US05071465

Reaction notes

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