Nitromethane → 3-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol

HRID 1627331Notes

Reaction equation

HRID 1627331 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F-].[K+].[CH3:18][N+:19]([O-:21])=[O:20]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]([OH:13])[CH2:18][N+:19]([O-:21])=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 522689Potassium FluorideHCID 592591132-(3,4-Dimethoxyphenyl)-2-methylpropanal

Product 1

HCID 667407963-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-olYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3,4-dimethoxyphenyl)-2-methylpropanal (1.0 g, 4.8 mmol) in EtOH (30 mL) were added KF (335 mg, 5.8 mmol) and CH3NO2 (1.56 mL, 28.8 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated, diluted with EtOAc, and washed with brine. The organic layer was dried over MgSO4, filtered and concentrated to give 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol (1.25 g, 97%). 1H NMR (400 MHz, CDCl3) δ 6.91-6.84 (m, 3H), 4.44 (m, 1H), 4.24 (d, 2H), 3.90 (s, 3H), 3.88 (s, 3H), 2.38 (d, 1H), 1.40 (s, 3H), 1.38 (s, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f24fcd48f1c94012aebd3d4e53406754
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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