Acetic Acid → HCID 22227836, compound

HRID 1744212Notes

Reaction equation

HRID 1744212 reaction equation
[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(OO)(=[O:16])C.C(O)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]2[CH2:11][O:16]2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6585Peracetic AcidHCID 5775311-(Tert-butoxy)-4-ethenylbenzene

Product 1

HCID 22227836HCID 22227836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butoxystyrene (17.6 g, 100 mmol) in methylene chloride (200 mL) cooled in an ice bath is added a solution of 32% peracetic acid in acetic acid (31.5 mL, 150 mmol). The mixture is stirred at rt overnight and quenched by addition of saturated sodium bicarbonate solution. The organic phase is separated, washed with sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. Chromatography on silica gel provides 2-(4-tert-butoxyphenyl)oxirane.

Workup

  1. customquenched by addition of saturated sodium bicarbonate solution
  2. customThe organic phase is separated
  3. washwashed with sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-11cf521af01d4ba485a080054d10fc79
Source dataset
uspto-grants-2006_03
Patent number
US07015217B2

Reaction notes

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