Allyl bromide → 1,3-Dinitro-5-{[(prop-2-en-1-yl)oxy]methyl}benzene

HRID 1885420Notes

Reaction equation

HRID 1885420 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2].[CH2:15](Br)[CH:16]=[CH2:17].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>[CH2:17]([O:8][CH2:7][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=1)[CH:16]=[CH2:15]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 1169783,5-Dinitrobenzyl alcohol

Product 1

HCID 198751771,3-Dinitro-5-{[(prop-2-en-1-yl)oxy]methyl}benzeneYield 80%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

20.0 g (101 mmol) of 3,5-dinitrobenzyl alcohol, 22 ml (254 mmol) of allyl bromide and 2.0 g (5.89 g) of tetrabutylamonium hydrogensulfate were dissolved in 100 ml of tetrahydrofuran, and a solution of 8.0 g (200 mmol) of sodium hydroxide as dissolved in 16 ml of water was added thereto and stirred overnight at room temperature. The reaction solution was extracted with diethyl ether and the organic phase was taken out and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product, which was then purified by column chromatography with silica gel (using a developer of chroroform/hexane=1/1). As a result, 19.1 g of 3,5-dinitrobenzyl allyl ether having a structural formula of: ##STR32## was obtained as a yellow oil. Yield: 80%. The product was identified to have the above-mentioned structure by the following IR spectrum, 1H-NMR spectrum and elementary analysis.

Workup

  1. additionwas added
  2. extractionThe reaction solution was extracted with diethyl ether
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto obtain a crude product, which
  6. customwas then purified by column chromatography with silica gel (

Sources & evidence

ORD record
ord-b5988b6b27db46ba9424d6743dcbbd6b
Source dataset
uspto-grants-1992_09
Patent number
US05144078

Reaction notes

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