Sulfuric Acid → 1,1-Bis(2-methoxyphenyl)ethene

HRID 466921Notes

Reaction equation

HRID 466921 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])(O)[CH3:10].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>CCOCC>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[CH2:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 144182001,1-Bis(2-methoxyphenyl)ethanol

Product 1

HCID 46392831,1-Bis(2-methoxyphenyl)etheneYield 58.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-Bis(2-methoxyphenyl)ethanol (25.6 g) was combined with 250 ml of acetic anhydride and the mixture was heated at reflux for 4 hours. A drop of concentrated sulfuric acid was added and the heating continued for 10 min. The opaque brown mixture obtained was allowed to cool and was diluted with ether. The resulting solution was extracted twice with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a brownish-black solid. This was recrystallized from methanol to obtain 14.0 g of the title compound as tan crystals melting at 88°-90° C. The proton NMR spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe opaque brown mixture obtained
  4. temperatureto cool
  5. extractionThe resulting solution was extracted twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customto obtain a brownish-black solid
  10. customThis was recrystallized from methanol

Sources & evidence

ORD record
ord-54f8666d9d6c47a9a48351c12bdce43e
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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