m-Chloroperbenzoic acid → HCID 22929986, compound

HRID 1296021Notes

Reaction equation

HRID 1296021 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]([O:21][CH2:22][O:23][CH3:24])=[C:17]([CH:20]=1)C=O>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]([O:21][CH2:22][O:23][CH3:24])=[C:17]([OH:9])[CH:20]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22930064HCID 22930064, compound

Product 1

HCID 22929986HCID 22929986, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

After adding 70% mCPBA (25 g) to a solution of 5-bromo-3-(tert-butyl)-2-(methoxymethoxy)benzaldehyde (30 g, 97 mmol) in methylene chloride (200 ml), the mixture was stirred at 50° C. for 2 hours. The organic layer was washed with a saturated sodium thiosulfate solution and saturated sodium hydrogencarbonate solution and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (17 g) as a light yellow oil.

Workup

  1. washThe organic layer was washed with a saturated sodium thiosulfate solution and saturated sodium hydrogencarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a429d06c88654d5bb08064cdd4ee7888
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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