Acetic Acid → HCID 582928, compound

HRID 1265980Notes

Reaction equation

HRID 1265980 reaction equation
[Br:1][C:2]1(Br)[CH2:4][C:3]1([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C>CO.[Zn]>[Br:1][CH:2]1[CH2:4][C:3]1([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 308177(2,2-Dibromo-1-methylcyclopropyl)benzene

Product 1

HCID 582928HCID 582928, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6.40 g (0.0221 mol) of 2,2-dibromo-1-methyl-1-phenylcyclopropane in 22 g of methanol was added 2.16 g (0.0360 mol) glacial acetic acid and 2.11 g (0.0323 mol) of zinc dust. After stirring at room temperature for 4 hours, the solvent was removed it vacuo. To the resulting residue hexanes and water were added. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 3.24 g of 2-bromo-1-methyl-1-phenylcyclopropane as an oil which was used without further purification.

Workup

  1. customthe solvent was removed it vacuo
  2. additionTo the resulting residue hexanes and water were added
  3. customThe resulting mixture was transferred to a separatory funnel
  4. customthe phases were separated
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-a9f9f9e9dfc24f688891fa52407d6208
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

Loading…