m-Chloroperbenzoic acid → HCID 57256524, compound

HRID 2097462Notes

Reaction equation

HRID 2097462 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)C=O.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([OH:22])[CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 197016265-Bromo-2-(methoxymethoxy)benzaldehyde

Product 1

HCID 57256524HCID 57256524, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 660 ml of dichloromethane solution containing 27.9 g (0.11 mol) of 5-bromo-2-methoxymethoxybenzaldehyde obtained in Reference example 5-(a) was added 42.9 g (0.132 mol) of m-chloroperbenzoic acid (purity: 53%), and the mixture was stirred at room temperature for 3 days. After completion of the reaction, the precipitated solid was removed from the reaction suspension by filtration, 97 ml of 2M aqueous sodium thiosulfate solution was added to the filtrate, and the mixture was stirred at room temperature for 2 hours. The organic layer after separation was concentrated under reduced pressure and the obtained solid was dissolved in diethyl ether. The solution was washed successively with 1M aqueous sodium thiosulfate solution, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 20.3 g of the title compound as a colorless oil. (Yield: 79%)

Workup

  1. customAfter completion of the reaction
  2. customthe precipitated solid was removed from the reaction suspension by filtration, 97 ml of 2M aqueous sodium thiosulfate solution
  3. additionwas added to the filtrate
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. customThe organic layer after separation
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionthe obtained solid was dissolved in diethyl ether
  8. washThe solution was washed successively with 1M aqueous sodium thiosulfate solution
  9. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionthe fractions containing the desired compound
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-27b445699b0f4d4d83ced50538fc1625
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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