Methyl iodide → Methyl tropate

HRID 1383381Notes

Reaction equation

HRID 1383381 reaction equation
[C:1]([OH:12])(=[O:11])[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH2:13](Cl)Cl.C1CCN2C(=NCCC2)CC1.CI>C1(C)C=CC=CC=1.O>[CH3:13][O:11][C:1](=[O:12])[CH:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 10726Tropic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 239086Methyl tropateYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of tropic acid (5.0 g, 30 mmol) in toluene:CH2Cl2 (150 mL; 2:1) was added DBU (4.6 g; 30 mmol), followed by MeI (4.3 g; 30 mmol). The mixture was stirred overnight, water was added and the phases were allowed to separate. The water phase was extracted wit h ether, and the combined organic phase was washed with NaHCO3(aq, HCe/aq and water, dried was Na2SO4) and concentrated to yield 0.95 g (18%) of the sub-title compound.

Workup

  1. customto separate
  2. extractionThe water phase was extracted wit h ether
  3. washthe combined organic phase was washed with NaHCO3(aq, HCe/aq and water, dried was Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe02bfef8b80444ba8f9a70d43435926
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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