Acetic Acid → 2-(2-Methoxyphenyl)oxirane

HRID 562948Notes

Reaction equation

HRID 562948 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])=[CH2:2].C(O)(=[O:13])C.BrN1C(=O)CCC1=O.[OH-].[Na+]>O1CCOCC1.O>[CH3:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH:1]1[CH2:2][O:13]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 611532-VinylanisoleHCID 67184N-bromobutanimide

Product 1

HCID 113555722-(2-Methoxyphenyl)oxiraneYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2-vinyl anisole (5.0 g, 0.037 mol) and acetic acid (2.1 mL, 37 mmol) in dioxane (33 ml) and H2O (78 ml) at 0° C. was added N-bromosuccinimide (7.30 g, 40.1 mmol) in three portions. The reaction was allowed to warm to R.T. and after 1 hour, 2M NaOH (50 ml) was added. The reaction was left to stir at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 7.56 g slightly tinted oil. This was dissolved in dioxane, 2N NaOH was added and the reaction was stirred at RT overnight. Repeated aqueous work-up gave 5.60 g of the title compound as a nearly colorless oil.

Workup

  1. waitThe reaction was left
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give 7.56 g slightly tinted oil
  9. stirringthe reaction was stirred at RT overnight

Sources & evidence

ORD record
ord-0afc455eb0cf42cbb134badfcb86b2dd
Source dataset
uspto-grants-2011_11
Patent number
US08067450B2

Reaction notes

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