Nitromethane → trans-4-Methoxy-beta-nitrostyrene

HRID 1685325Notes

Reaction equation

HRID 1685325 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:14]/[N+:11]([O-:13])=[O:12])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 697963trans-4-Methoxy-beta-nitrostyrene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cool (0° C.), stirred solution of 4-anisaldehyde (1.75 mL, 14.3 mmol), nitromethane (2.0 mL, 36.9 mmol) in MeOH (6.0 mL) was added NaOH (1M, 40 mL), and allowed to warm to room temperature. After 2.5 hours, ice water was added with stirring, extracted with DCM (3×), the combined extracts were dried (MgSO4), filtered, concentrated and purified on Biotage Horizon to provide the product as a solid: 1H NMR (400 MHz, CDCl3) δ ppm: 7.97 (1H, d, J=13.64 Hz), 7.51 (1H, d, J=13.64 Hz), 7.50 (1H, d, J=8.84 Hz), 6.95 (2H, d, J=8.84 Hz), 3.86 (3H, s).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with DCM (3×)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on Biotage Horizon

Sources & evidence

ORD record
ord-347940af409348a9af43ff783f282a1a
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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