Iodine → 1,1-Bis-(3-methoxyphenyl)ethene

HRID 48466Notes

Reaction equation

HRID 48466 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.II>C(O)(=O)C.O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH2:10])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 807IodineHCID 227434361,1-Bis(3-methoxyphenyl)ethanol

Product 1

HCID 99918831,1-Bis-(3-methoxyphenyl)etheneYield 96.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5.28 g (20 mmoles) of 1,1-bis(3-methoxyphenyl)ethanol are dissolved in 30 mL of glacial acetic acid. A catalytical amount of iodine is added and the solution refluxed for about 5-15 minutes or until the dehydration is complete. The progress of the reaction is monitored by TLC on silica (5% EtOAc in hexanes). The burgundy red solution is diluted with water (100 mL) and the product extracted with ether (2-3 extractions with 10 mL portions). The combined ethereal extracts are washed consecutively with water (into which a spatula tip of sodium metabisulfite was added) and 10% sodium carbonate, dried over anh. K2CO3 and evaporated to yield 4.63 g (96%) of the title compound. 1H NMR (CDCl3): 6.8-7.3 (m, ArH, 8H), 5.45(s, C═CH2, 2H), 3.75 (s, OCH3, 6H).

Workup

  1. temperaturethe solution refluxed for about 5-15 minutes or until the dehydration
  2. extractionthe product extracted with ether (2-3 extractions with 10 mL portions)
  3. washThe combined ethereal extracts are washed consecutively with water (into which a spatula tip of sodium metabisulfite
  4. additionwas added) and 10% sodium carbonate
  5. dry with materialdried over anh. K2CO3
  6. customevaporated

Sources & evidence

ORD record
ord-81aab6d4c15f49c5ad2ceda9e2a7edf0
Source dataset
uspto-grants-2004_03
Patent number
US06703504B2

Reaction notes

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