Toluene → 2,2-Bis(2'-methoxyphenyl)propane

HRID 466922Notes

Reaction equation

HRID 466922 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[CH2:10].[C:19]1(C)C=CC=CC=1.C1(OC)C=CC=CC=1.COCCO[AlH2-]OCCOC.[Na+]>CCCCCC>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:19])[CH3:10]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7519AnisoleHCID 46392831,1-Bis(2-methoxyphenyl)etheneHCID 16684438Red-Al

Product 1

HCID 5787142,2-Bis(2'-methoxyphenyl)propane

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1,1-Bis(2-methoxyphenyl)ethene (15.6 g), toluene (35 ml) and anisole (35 ml) were combined in a flask and 35 ml of a 3.7M hexane solution of Red-Al was added. The mixture was heated to reflux with stirring whereupon it turned dark red. After 2 hours the heat was removed and the mixture was allowed to stir overnight. The excess hydride reagent was carefully quenched with 1.0N hydrochloric acid. The mixture was then diluted with ether and the ethereal solution separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a golden-brown oil. This was triturated with hexane to obtain 3.70 of the title compound. The proton and carbon NMR spectra were consistent with the assigned structure.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customAfter 2 hours the heat was removed
  4. stirringto stir overnight
  5. customThe excess hydride reagent was carefully quenched with 1.0N hydrochloric acid
  6. additionThe mixture was then diluted with ether
  7. customthe ethereal solution separated
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation under reduced pressure
  11. customto obtain a golden-brown oil
  12. customThis was triturated with hexane

Sources & evidence

ORD record
ord-54ea592d61eb4e96a7737c1eaf0d4b4c
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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