3-(Dimethylamino)phenol → HCID 20344286, compound

HRID 2049724Notes

Reaction equation

HRID 2049724 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11]

Participants

5

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 11430Potassium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 20344286HCID 20344286, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 27.5 g. (0.2 mole) of m-dimethylaminophenol, 94 g. (0.39 mole) of 1,6-dibromohexane, 53.8 g. of powdered anhydrous potassium carbonate and 350 ml. of acetone was heated at reflux under nitrogen for two days. The reaction mixture was concentrated in vacuo and the residue partitioned between water and methylene dichloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was distilled to remove unreacted 1,6-dibromohexane (b.p. 63° C., 0.2 mm.). The remaining material was dissolved in 5% sulfuric acid by warming on a steam bath, then filtered, cooled and made basic with sodium hydroxide. The product was extracted with chloroform, washed with water, dried over magnesium sulfate and concentrated to a reddish brown oil, 52.4 g.

Workup

  1. additionA mixture of 27.5 g
  2. temperatureat reflux under nitrogen for two days
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between water and methylene dichloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe residue was distilled
  9. customto remove unreacted 1,6-dibromohexane (b.p. 63° C., 0.2 mm.)
  10. dissolutionThe remaining material was dissolved in 5% sulfuric acid
  11. temperatureby warming on a steam bath
  12. filtrationfiltered
  13. temperaturecooled
  14. extractionThe product was extracted with chloroform
  15. washwashed with water
  16. dry with materialdried over magnesium sulfate
  17. concentrationconcentrated to a reddish brown oil, 52.4 g

Sources & evidence

ORD record
ord-a191a85247c544d4be4241523729e75a
Source dataset
uspto-grants-1980_04
Patent number
US04198436

Reaction notes

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