Acrylonitrile → HCID 54468138, compound

HRID 1419218Notes

Reaction equation

HRID 1419218 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[OH-].[Na+].[C:15](#[N:18])[CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[OH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:8]=1[CH2:17][CH2:16][C:15]#[N:18]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 54468138HCID 54468138, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To 44.8 g of 6-bromo-2-naphthol were added 120 ml of toluene and 8.8 g of sodium hydroxide, followed by stirring at 65° C. for 30 minutes. Then, thereto was added dropwise 11.4 g of acrylonitrile at 80° C., followed by stirring at the same temperature for 3.5 hours. After left for cooling, the toluene layer was decanted, and to the residue was added 240 ml of water. A small amount of insoluble matter was filtered off, and to the filtrate was added 140 ml of 5% hydrochloric acid. The precipitate was collected by filtration and sufficiently washed with water. The resulting crude product was recrystallized from ethanol to obtain 30.7 g of the desired product.

Workup

  1. stirringby stirring at the same temperature for 3.5 hours
  2. waitAfter left
  3. temperaturefor cooling
  4. customthe toluene layer was decanted
  5. additionto the residue was added 240 ml of water
  6. filtrationA small amount of insoluble matter was filtered off
  7. additionto the filtrate was added 140 ml of 5% hydrochloric acid
  8. filtrationThe precipitate was collected by filtration
  9. washsufficiently washed with water
  10. customThe resulting crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-6ca3338166144fbc994503deb3d92364
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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