Methyl iodide → 2,2-Bis(2-methoxyphenyl)butane

HRID 466924Notes

Reaction equation

HRID 466924 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[Li].CI.O1CC[CH2:25][CH2:24]1>CCOCC>[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])([CH2:24][CH3:25])[CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 8028TetrahydrofuranHCID 46392831,1-Bis(2-methoxyphenyl)etheneHCID 178418348HCID 178418348, compound

Product 1

HCID 198126932,2-Bis(2-methoxyphenyl)butane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-Bis(2-methoxyphenyl)ethene (5.6 g) was dissolved in 25 ml of tetrahydrofuran and 25 ml of a 1.3M solution of methyl lithium in ether was added dropwise with stirring. The solution became dark red and exothermed. After 2 hours, 5.0 ml of methyl iodide was added slowly with stirring. The solution again exothermed. When all of the methyl iodide had been added the starting material was found to be completely consumed and replaced by a single product by gas-liquid chromatography. About 300 ml of ether was added and the resulting solution was extracted with 100 ml of water and then 100 ml of brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 5.46 g (88 percent of theory) of the title compound as a pale yellow crystalline solid melting at 49°-52° C. The proton and carbon NMR and infrared spectra were consistent with the assigned structure.

Workup

  1. stirringwith stirring
  2. customto be completely consumed
  3. additionAbout 300 ml of ether was added
  4. extractionthe resulting solution was extracted with 100 ml of water
  5. dry with material100 ml of brine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-354f6e1c48684377ac42444c54eaf393
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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