Hydrochloric Acid → 1,3-dimethoxy-5-(2-nitroethenyl)benzene

HRID 1632575Notes

Reaction equation

HRID 1632575 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[N+:13]([CH3:16])([O-:15])=[O:14].[OH-].[Na+].Cl>O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[CH:16][N+:13]([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 6106161,3-dimethoxy-5-(2-nitroethenyl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 34.5 g. (0.208 mole) 3,5-dimethoxybenzaldehyde and 12.68 g. (0.208 mole) nitromethane in 40 ml. methanol was cooled to 0° C. under a nitrogen atmosphere. To this was added dropwise a cold solution of 8.43 g. (0.211 mole) sodium hydroxide in 30 ml. water and stirring continued at 0° C. for 15 minutes after the addition was completed. The mixture was diluted with ice-water and added slowly to a solution of 40 ml. concentrated hydrochloric acid in 60 ml. water. The precipitated product (44 g.) was collected by filtration and recrystallized from methanol to give 28.6 g., M.P. 132° C. J. Org. Chem., 27, 376 (1976) reported M.P. 133.5°-134.5° C.

Workup

  1. additionTo this was added dropwise a cold solution of 8.43 g
  2. additionafter the addition
  3. additionadded slowly to a solution of 40 ml
  4. filtrationThe precipitated product (44 g.) was collected by filtration
  5. customrecrystallized from methanol
  6. customto give 28.6 g

Sources & evidence

ORD record
ord-06409e75dbb3495f8f8461452b1061c6
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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