Methyl iodide → Methyl 4-ethenylbenzoate

HRID 744988Notes

Reaction equation

HRID 744988 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2].N12CCCN=C1CCCC[CH2:13]2.IC.C(OCC)(=O)C>C(#N)C>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 140984-Vinylbenzoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 583124Methyl 4-ethenylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-vinylbenzoic acid (Aldrich, 2.18 g, 14.7 mmol) in anhydrous acetonitrile (14.0 mL) was added 1.8-diazabicyclo [5.4.0]undec-7-ene (Aldrich, 2.46 g, 16.2 mmol) and iodomethane (Aldrich, 3.13g, 22.1 mmol) at 0° C. The reaction mixture was then warmed to room temperatue and allowed to stir for 3 h. Ethyl acetate (100 mL) was added to the mixture and the solution was washed with brine (50 mL). The organic phase was then separated and concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane) to give 1.05 g (Y: 44%) of the title product. 1H-NMR (CDCl3): δ8.00 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 6.76 (m, 1H), 5.87 (d, J=17.6 Hz, 1H), 5.38 (d, J=11.0 Hz, 1H), 3.91 (s, 3H); MS (DCI)m/e: 163 (MH+).

Workup

  1. temperatureThe reaction mixture was then warmed to room temperatue
  2. washthe solution was washed with brine (50 mL)
  3. customThe organic phase was then separated
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b8a0e001947f4233b19756ff7ae38a25
Source dataset
uspto-grants-1996_09
Patent number
US05559248

Reaction notes

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