Hydrochloric Acid → 2-Methoxy-1-(2-nitroethenyl)naphthalene

HRID 893085Notes

Reaction equation

HRID 893085 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=O.[N+:15]([CH3:18])([O-:17])=[O:16].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=[CH:18][N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 793522-Methoxy-1-naphthaldehyde

Product 1

HCID 8966262-Methoxy-1-(2-nitroethenyl)naphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxy-1-naphthaldehyde (1862 mg, 10 mmol) and nitromethane (610 mg, 10 mmol) in methanol (200 ml) is stirred at room temperature until the solids dissolved. The solution is cooled to about 0° C. and a 30% NaOH solution (2 ml, 20 mmol) is added dropwise over 30 min. The resulting solution is added slowly at 60° C. to a 35% HCl solution (200 ml). The amorphous solid that formed is filtered and washed with water. The crude product is recrystallized from ethanol to give pure title compound in 80% yield (1835 mg).

Workup

  1. dissolutiondissolved
  2. temperatureThe solution is cooled to about 0° C.
  3. customThe amorphous solid that formed
  4. filtrationis filtered
  5. washwashed with water
  6. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-d2af4e85f96c4c668b50a726aa083c54
Source dataset
uspto-grants-1992_06
Patent number
US05122537

Reaction notes

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