3-(Dimethylamino)phenol → HCID 20312681, compound

HRID 2420026Notes

Reaction equation

HRID 2420026 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH3:5][N:6]([CH3:14])[C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[Na]>C(O)(=O)C>[CH3:5][N:6]([CH3:14])[C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:3][CH2:2][C:1]#[N:4]

Participants

5

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 7855AcrylonitrileHCID 5360545Sodium

Product 1

HCID 20312681HCID 20312681, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 407 g (7.68 moles) portion of acrylonitrile and 500 g (3.65 moles) of m-dimethylaminophenol were placed in a 3-l, 3-necked flask equipped with a stirrer and reflux condenser with a drying tube. The solution was treated with 4 g (0.17 mole) of metallic sodium, over 0.7 hr., with an observed temperature rise from 10° to 24°. The reaction mixture was heated to reflux over 0.8 hr., refluxed for 22 hrs., cooled, treated with 11 ml of glacial acetic acid and the excess acrylonitrile removed under reduced pressure. The residue was taken up in 3.8-l of ether, decanted from a purple resinous material, stored over Darco overnight and filtered. The filtrate was stripped of ether under reduced pressure to give 590 g (80%) of the desired nitrile (brown).

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser with a drying tube
  3. customfrom 10° to 24°
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux over 0.8 hr
  6. temperature, refluxed for 22 hrs
  7. temperature, cooled
  8. customthe excess acrylonitrile removed under reduced pressure
  9. customdecanted from a purple resinous material
  10. customstored over Darco overnight
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d0acd4ce94a24cfba805dd2a4ee0b26b
Source dataset
uspto-grants-1978_08
Patent number
US04108872

Reaction notes

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