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

HRID 249371Notes

Reaction equation

HRID 249371 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)-4ethenyl-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 HPLC 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 HPLC

Sources & evidence

ORD record
ord-3d1973c7b2614b3fa535ae15d4b90b33
Source dataset
uspto-grants-1993_05
Patent number
US05214105

Reaction notes

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