2-Methyl-2-nitro-1-propanol → 2-Methyl-2-nitro-1-benzyloxypropane

HRID 636745Notes

Reaction equation

HRID 636745 reaction equation
[CH3:1][C:2]([N+:6]([O-:8])=[O:7])([CH3:5])[CH2:3][OH:4].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH3:1][C:2]([N+:6]([O-:8])=[O:7])([CH3:5])[CH2:3][O:4][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 64422-Methyl-2-nitro-1-propanolHCID 7498Benzyl Bromide

Product 1

HCID 212556982-Methyl-2-nitro-1-benzyloxypropaneYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-methyl-2-nitro-1-propanol (2.3975 g, 20.13 mmol) and Ag2O (4.6385 g, 20.02 mmol) in DMF (25 ml) was added benzyl bromide (2.65ml, 22.28 mmol) and stirred for 48 hours. The mixture was filtered and the filtrate was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate/hexane=1/1 and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (toluene) to give the title compound (639.4 mg; 15%).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was added to 5% KHSO4 aqueous solution
  3. extractionextracted three times with ethyl acetate/hexane=1/1
  4. dry with materialdried over MgSO4
  5. concentrationThe mixture was concentrated
  6. custompurified by silica gel chromatography (toluene)

Sources & evidence

ORD record
ord-0c3531021adb42db8a83f78644452a53
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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