m-Chloroperbenzoic acid → HCID 90404026, compound

HRID 1464874Notes

Reaction equation

HRID 1464874 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH2:10][OH:11])[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH2:10][OH:11])[CH:2]1[O:21][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90404088HCID 90404088, compound

Product 1

HCID 90404026HCID 90404026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-allyloxy-2-nitrobenzyl alcohol (7.3 g, 35 mmol) and m-chloroperoxybenzoic acid (77 wt. %, 9.4 g, 42 mmol) were dissolved in dichloromethane and refluxed until the allyl peaks disappeared from the 1H-NMR spectrum (approximately 48 hours). The reaction was then washed with aqueous sodium carbonate twice, water three times and then dried over sodium sulfate. The solvent was partially removed by rotary evaporation and then poured into hexanes to precipitate the product. The resulting solid was collected by suction filtration and was used in the next step without further purification.

Workup

  1. custompeaks disappeared from the 1H-NMR spectrum (approximately 48 hours)
  2. washThe reaction was then washed with aqueous sodium carbonate twice
  3. dry with materialwater three times and then dried over sodium sulfate
  4. customThe solvent was partially removed by rotary evaporation
  5. additionpoured into hexanes
  6. customto precipitate the product
  7. filtrationThe resulting solid was collected by suction filtration
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-f425b498168f4341b45de38d74c006ef
Source dataset
uspto-grants-2015_04
Patent number
US08999623B2

Reaction notes

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