Acetaminophen → 4,4'-[Decane-1,10-diylbis(oxy)]dianiline

HRID 2417557Notes

Reaction equation

HRID 2417557 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br.[OH:13][C:14]1[CH:23]=[CH:22][C:17]([NH:18]C(=O)C)=[CH:16][CH:15]=1.[OH-:24].[Na+]>C(O)C>[NH2:18][C:17]1[CH:22]=[CH:23][C:14]([O:24][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:18])=[CH:22][CH:23]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 14798Sodium HydroxideHCID 2214831,10-Dibromodecane

Product 1

HCID 135806854,4'-[Decane-1,10-diylbis(oxy)]dianiline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 g (0.1 mole) of 1,10-dibromodecane and 38 g (0.25 mole) of p-hydroxyacetanilide were heated under reflux for 8 hours in the presence of 12 g of NaOH using ethanol. After the reaction, the resulting mixture was poured into ice water and the precipitate formed was collected, followed by washing with heated ethanol. The remaining brown crystal without purification was added in a mixed solvent of 100 ml of conc. HCl and 200 ml of ethanol and the system was heated under reflux for 2 hours. A solid remained after removing the solvent under reduced pressure which was dissolved in 2 l of ice water, and a 20% NaOH aqueous solution was added thereto to neutralize. The thus-precipitated solid was collected and recrystallized from ethanol to a pale brown grained crystal having a melting point of 70° to 71° C. at a yield of 18 g (51%). The crystal was identified as 1,10-bis(p-aminophenoxy)decane from its NMR spectrum and IR spectrum.

Workup

  1. customAfter the reaction
  2. customthe precipitate formed
  3. customwas collected
  4. washby washing with heated ethanol
  5. customThe remaining brown crystal without purification
  6. additionwas added in a mixed solvent of 100 ml of conc. HCl and 200 ml of ethanol
  7. temperaturethe system was heated
  8. temperatureunder reflux for 2 hours
  9. customafter removing the solvent under reduced pressure which
  10. dissolutionwas dissolved in 2 l of ice water
  11. additiona 20% NaOH aqueous solution was added
  12. customThe thus-precipitated solid was collected
  13. customrecrystallized from ethanol to a pale

Sources & evidence

ORD record
ord-6e2a9981313d4893a13a4d3cc2b173ed
Source dataset
uspto-grants-1984_09
Patent number
US04469621

Reaction notes

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