Benzaldehyde → Beta-Nitrostyrene

HRID 1367628Notes

Reaction equation

HRID 1367628 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([CH3:12])([O-:11])=[O:10].[OH-].[Na+].Cl.O>CO>[N+:9]([CH:12]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 7626Beta-Nitrostyrene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Benzaldehyde (2, 52.35 g, 0.493 mol) and nitromethane (30.11 g, 0.493 mol) were dissolved in methanol (100 mL) in a two-necked flask equipped with a thermometer and a pressure-equalizing dropping funnel. NaOH (25.6 g, 0.641 mol) in ice/water (50 mL) was added dropwise to the solution keeping the temperature below 15° C. A fine slurry formed during the addition and methanol was added to allow stirring. After the addition the slurry was diluted with ice/water and the resulting clear solution was added dropwise to a solution of conc. HCl/H2O (200/300 ml); a yellow precipitate was formed during the addition. The precipitate was filtered on a buchner funnel, washed with water and crystallized from methanol obtaining pure 3 (58.78 g, 80%). Yellow needles. M.p. 57-58° C.

Workup

  1. customequipped with a thermometer
  2. customthe temperature below 15° C
  3. additionwas added
  4. additionAfter the addition the slurry
  5. customa yellow precipitate was formed during the addition
  6. filtrationThe precipitate was filtered on a buchner funnel
  7. washwashed with water
  8. customcrystallized from methanol obtaining pure 3 (58.78 g, 80%)

Sources & evidence

ORD record
ord-9af218ca90434eaa9268d5a800283e4c
Source dataset
uspto-grants-2011_02
Patent number
US07893223B2

Reaction notes

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