Diethyl Ether → Ethylidenebisphenol

HRID 359187Notes

Reaction equation

HRID 359187 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])(O)[CH3:9].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.CCOCC>ClCCl.O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH3:9]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 198126961,1-Bis(2-hydroxyphenyl)ethanol

Product 1

HCID 13530914EthylidenebisphenolYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

1,1-Bis(2-hydroxyphenyl)ethanol (8.57 g) dissolved in 40 ml of dichloromethane was cooled with an ice bath and to this was added sequentially with stirring 3.70 ml of trifluoroacetic acid in 20 ml of dichloromethane and (dropwise) 7.67 ml of triethylsilane in 20 ml of dichloromethane. The mixture was allowed to warm to room temperature and react for another 2 hours. Ether and water were added and the phases separated. The organic phase was extracted with several small portions of 2N sodium hydroxide and the extracts were combined and acidified with hydrochloric acid. The resulting mixture was extracted with ether and the ether extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 6.10 g of the title compound as a brown oil.

Workup

  1. temperaturewas cooled with an ice bath
  2. additionto this was added sequentially
  3. customreact for another 2 hours
  4. customthe phases separated
  5. extractionThe organic phase was extracted with several small portions of 2N sodium hydroxide
  6. extractionThe resulting mixture was extracted with ether
  7. extractionthe ether extract
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5e02533add6f4aa68abc3244f3f8c90b
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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