Reaction #1552056

Reaction equation

5-allyloxy-2-nitrobenzyl alcohol

m-chloroperoxybenzoic acid

→

5-glycidyloxy-2-nitrobenzyl alcohol

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherpeaks disappeared from the 1H-NMR spectrum (approximately 48 hours)
2. 2
   WashThe reaction was then washed with aqueous sodium carbonate twice
3. 3
   Dryingwater three times and then dried over sodium sulfate
4. 4
   OtherThe solvent was partially removed by rotary evaporation
5. 5
   workup.ADDITIONpoured into hexanes
6. 6
   Otherto precipitate the product
7. 7
   FiltrationThe resulting solid was collected by suction filtration
8. 8
   Otherwas used in the next step without further purification

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.

Source