Methyl iodide → 1-Ethenyl-4-(2-methoxypropan-2-yl)benzene

HRID 248356Notes

Reaction equation

HRID 248356 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].I[CH3:14].[H-].[Na+].[H][H]>O1CCCC1.O>[CH3:14][O:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH2:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 12542438Benzenemethanol, 4-ethenyl-α,α-dimethyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 184004161-Ethenyl-4-(2-methoxypropan-2-yl)benzeneYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.10 g of 1-(1-hydroxy-1-methylethyl)-4-ethenyl-benzene in 25 ml of dry tetrahydrofuran containing 7 g of iodomethane was heated to 40°-50° C. and treated portionwise in a dry atmosphere with 1 g of a sodium hydride dispersion (60% NaH in mineral oil) under rapid stirring. Reaction was accompanied by evolution of hydrogen. Once the addition was complete stirring was continued for another 30 minutes. The cooled mixture was then poured into water and extracted with ether. The organic phase was then washed with brine, dried over magnesium sulfate and evaporated to yield a crude product which was purified by preparative HPLO using ethyl acetate-hexane as the eluent to afford 2.25 g (51%) of the desired methyl ether.

Workup

  1. customReaction
  2. additionOnce the addition
  3. extractionextracted with ether
  4. washThe organic phase was then washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto yield a crude product which
  8. customwas purified by preparative HPLO

Sources & evidence

ORD record
ord-bb1a4b3e50bd490ea74bd707dc78c38b
Source dataset
uspto-grants-1993_05
Patent number
US05210148

Reaction notes

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