Nitromethane → 4-Methoxy-beta-nitrostyrene

HRID 424286Notes

Reaction equation

HRID 424286 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+].Cl.O>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:14][N+:11]([O-:13])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 21885828Hydrate;hydrochloride

Product 1

HCID 2298434-Methoxy-beta-nitrostyrene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

p-Methoxybenzaldehyde (11.19 g, 82.2 mmol) and nitromethane (5.0 g, 82.2 mmol) were dissolved in methanol (20 mL) in a two-necked flask equipped with a thermometer and a pressure-equalizing dropping funnel. NaOH (4.27 g, 0.107 mol) in ice/water (10 mL) was added dropwise to the solution keeping the temperature below 15° C. A fine slurry formed during addition and additional methanol was added to allow efficient stirring. After the addition the reaction mixture was diluted with ice/water and the resulting clear solution was added dropwise to a solution of HCl/H2O (40 mL/60 mL); a yellow precipitate formed during the addition. The precipitate was filtered on a buchner funnel and crystallized from methanol obtaining 4-methoxy-β-nitrostirene (10.66 g, 72%). Yellow needles. M.p. 57-58° C. ESI-MS: 180 (MH±); (Calc. for C9H9NO3: 179 u.m.a.).

Workup

  1. customequipped with a thermometer
  2. customthe temperature below 15° C
  3. additionwas added
  4. additionAfter the addition the reaction mixture
  5. customa yellow precipitate formed during the addition
  6. filtrationThe precipitate was filtered on a buchner funnel
  7. customcrystallized from methanol
  8. customobtaining 4-methoxy-β-nitrostirene (10.66 g, 72%)

Sources & evidence

ORD record
ord-87d1d61c7459494ea25f92ab01132837
Source dataset
uspto-grants-2012_01
Patent number
US08105567B2

Reaction notes

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