m-Chloroperbenzoic acid → HCID 68586567, compound

HRID 242160Notes

Reaction equation

HRID 242160 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:8][N:7]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:27])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:8][N+:7]=1[O-:27])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 59278627HCID 59278627, compound

Product 1

HCID 68586567HCID 68586567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.74 g of the crude product from example 25A is dissolved in 3.4 ml of dry dichloromethane, and 0.74 g (3.21 mmol) of meta-chloroperbenzoic acid is added a little at a time. The reaction mixture is stirred at RT for 8 h, and 2 ml of saturated aqueous sodium bicarbonate solution are then added. With stirring, more sodium bicarbonate powder (about 0.4 g) is added until the evolution of gas has ceased. The aqueous phase is extracted twice with in each case 5 ml of dichloromethane, and the combined organic phases are dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product that remains is used directly for the subsequent reaction.

Workup

  1. stirringWith stirring
  2. extractionThe aqueous phase is extracted twice with in each case 5 ml of dichloromethane
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. customAfter removal of the solvent
  5. customon a rotary evaporator
  6. customthe crude product that remains is used directly for the subsequent reaction

Sources & evidence

ORD record
ord-accbef4c44564cd1bb7e71704fbf5590
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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