Ethanol → 2-(3-Methylphenyl)-2-nitropropane-1,3-diol

HRID 64440Notes

Reaction equation

HRID 64440 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N+:9]([O-:11])=[O:10])[CH:3]=1.[OH-:12].[Na+].[CH2:14]=O.[CH2:16]([OH:18])C>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([N+:9]([O-:11])=[O:10])([CH2:16][OH:18])[CH2:14][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 712Formaldehyde2×HCID 14798Sodium Hydroxide2×HCID 112865651-Methyl-3-(nitromethyl)benzene

Product 1

HCID 867134582-(3-Methylphenyl)-2-nitropropane-1,3-diol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixed solution of 1.55 g of 1-methyl-3-(nitromethyl)benzene in 15 ml of ethanol and 6 ml of dioxane were added 0.05 ml of a 1 M aqueous sodium hydroxide solution and 1.89 ml of a 37% aqueous formalin solution, followed by stirring for 15 hours. 0.05 ml of a 1 M aqueous sodium hydroxide solution and 0.83 ml of a 37% aqueous formalin solution were added thereto, followed by stirring at 50° C. for 2 hours, and the solvent was evaporated under reduced pressure. To the obtained residue was added ethyl acetate, followed by washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.91 g of 2-(3-methylphenyl)-2-nitropropane-1,3-diol.

Workup

  1. stirringby stirring at 50° C. for 2 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue was added ethyl acetate
  4. washby washing with saturated brine
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff579edcad5a47e4b62f37b3a4aedc9d
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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