Ethanol → HCID 54074187, compound

HRID 1274524Notes

Reaction equation

HRID 1274524 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[O-2:13].[Al+3].[O-2].[O-2].[Al+3].Cl[CH2:19][C:20](Cl)=[O:21].[CH2:23]([OH:25])[CH3:24]>>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]2[C:20](=[O:21])[C:19](=[C:23]3[C:24](=[O:13])[C:7]4[CH:6]=[CH:5][C:4]([N:3]([CH2:11][CH3:12])[CH2:1][CH3:2])=[CH:9][C:8]=4[O:25]3)[O:10][C:6]=2[CH:5]=1)[CH3:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 6577Chloroacetyl chloride3×HCID 70623-(Diethylamino)phenolHCID 9989226Alumina2×

Product 1

HCID 54074187HCID 54074187, compound

Procedure

1.0 g (6.0 mmol) of 3-diethylamino-phenol is dissolved in 29 g of absolute ethanol with exclusion of moisture. 10 g of basic aluminium oxide are then allowed to trickle into the solution, with vigorous stirring. 0.7 g (6.0 mmol) of chloroacetyl chloride is added dropwise through an attached reflux condenser. The dark violet reaction mixture is heated to the boiling point under reflux, with vigorous stirring. After 2 hours, 1.0 ml (12 mmol) of chloroacetyl chloride is added dropwise through the reflux condenser. After a further 30 minutes, a further 1.5 ml (18 mmol) of chloroacetyl chloride and 2 g of basic aluminium oxide are added. After 10 minutes, the reaction mixture becomes dark red in colour. The reaction mixture is left to stand at 60-70° C. for 60 hours. Finally, the mixture is filtered with suction through a G4 frit and the solid is washed several times with absolute ethanol until the wash solution is virtually colourless. The dark red organic phases are combined. The ethanol is stripped off on a rotary evaporator. 3 g of a dark red, highly viscous residue are obtained, this being purified by column chromatography over silica gel using chloroform as the mobile phase. The colorant is isolated as a red-violet fraction in the first runnings. After the solvent has been stripped off, the resulting dark red solid is dried under an oil pump vacuum at 95° C. for 5 hours.

Workup

  1. temperaturean attached reflux condenser
  2. temperatureThe dark violet reaction mixture is heated to the boiling point
  3. temperatureunder reflux, with vigorous stirring
  4. waitAfter a further 30 minutes
  5. waitAfter 10 minutes
  6. waitThe reaction mixture is left
  7. waitto stand at 60-70° C. for 60 hours
  8. filtrationFinally, the mixture is filtered with suction through a G4 frit
  9. washthe solid is washed several times with absolute ethanol until the wash solution
  10. customThe ethanol is stripped off on a rotary evaporator
  11. custom3 g of a dark red, highly viscous residue are obtained
  12. customthis being purified by column chromatography over silica gel
  13. customThe colorant is isolated as a red-violet fraction in the first runnings
  14. customthe resulting dark red solid is dried under an oil pump vacuum at 95° C. for 5 hours

Sources & evidence

ORD record
ord-0edccf7112e941ff815f83a8e8f72678
Source dataset
uspto-grants-2000_12
Patent number
US06156914

Reaction notes

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