Hydrochloric Acid → (E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene

HRID 1690899Notes

Reaction equation

HRID 1690899 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[N+:20]([CH3:23])([O-:22])=[O:21].Cl>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:23]/[N+:20]([O-:22])=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 10942334Sodium Methoxide2×

Product 1

HCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-benzyloxybenzaldehyde (1.0 g, 4.7 mmol) and sodium methoxide (28% methanol solution, 150 μL, 0.74 mmol) and methanol (10 mL) were added nitromethane (330 μL, 6.1 mmol) and sodium methoxide (28% methanol solution, 1.0 mL, 4.9 mmol) at 0° C., which was stirred for 10 minutes at room temperature. The reaction mixture was cooled to 0° C., and 5 N aqueous hydrochloric acid solution (20 mL) was added thereto at the same temperature. The reaction mixture was then stirred for 15 minutes at room temperature. The precipitated solids were filtered to obtain the title compound (1.2 g, 100%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was then stirred for 15 minutes at room temperature
  3. filtrationThe precipitated solids were filtered

Sources & evidence

ORD record
ord-f068eb7d2f7742f0bddabb8b5294996c
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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