Acetic Acid → 2-(3-Methoxyphenyl)oxirane

HRID 2274335Notes

Reaction equation

HRID 2274335 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1)=[CH2:2].C(O)(=[O:13])C.BrN1C(=O)CCC1=O.[OH-].[Na+]>O1CCOCC1.O>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH:1]2[CH2:2][O:13]2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 5841461-Ethenyl-3-methoxybenzene

Product 1

HCID 979032-(3-Methoxyphenyl)oxiraneYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-vinylanisole (5.0 g, 37.0 mmol) and acetic acid (2.1 mL, 37.0 mmol) in dioxane (33 mL) and H2O (78 mL) at 0° C. was added N-bromosuccinimide (7.30 g, 41.0 mmol) in three portions. The reaction was allowed to warm to RT and then 2M NaOH (50 mL) was added. The reaction was left to stir at RT overnight. The reaction mixture was then partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 5.60 g (100%) of the title compound as a slightly tinted oil.

Workup

  1. waitThe reaction was left
  2. customThe reaction mixture was then partitioned between water and EtOAc
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-82fa006b8aa94a1489eb0c32bc306885
Source dataset
uspto-grants-2015_09
Patent number
US09126959B2

Reaction notes

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