Water → 2-Methyl-2-nitro-1-(methoxymethoxy)propane
Reaction equation
[CH3:1][C:2]([N+:6]([O-:8])=[O:7])([CH3:5])[CH2:3][OH:4].[Li+].[Br-].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[CH3:24][O:25][CH2:26]OC>>[CH3:1][C:2]([N+:6]([O-:8])=[O:7])([CH3:5])[CH2:3][O:4][CH2:24][O:25][CH3:26]Participants
6
Procedure
To a solution of 2-methyl-2-nitro-1-propanol (366.8 mg, 3.08 mmol) and LiBr (60.8 mg, 0.700 mmol) in dimethoxymethane (5 ml) was added p-toluenesulfonic acid hydrate (56.3 mg, 0.296 mmol) and stirred for 24 hours. The mixture was added to water and extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=4/1) to give the title compound (382.7 mg; 76%).
Workup
- extractionextracted three times with ethyl acetate
- dry with materialdried over MgSO4
- concentrationThe mixture was concentrated
- custompurified by silica gel chromatography (hexane/ether=4/1)
Sources & evidence
- ORD record
- ord-65625b631df84f3c80df010961eff1d7
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194461B1
Reaction notes
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