Hydrochloric Acid → N-Octylaniline

HRID 1022366Notes

Reaction equation

HRID 1022366 reaction equation
C([N:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)C.Cl.[OH-].[K+]>O>[CH2:11]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66942989N-acetyl-N-octylaniline

Product 1

HCID 137788N-OctylanilineYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

To N-acetyl-N-octylaniline (48.4 g, 196 mmol) there was added 4N hydrochloric acid (100 mL) and the mixture heated to 100-110° C. and stirred at this temperature for 4 days. The reaction mixture was cooled to ambient temperature, diluted with water (100 mL), and hexanes (200 mL). The pH of the reaction mixture was brought to pH 14 by addition of 45% potassium hydroxide with cooling by an ice bath. The layers were separated and the aqueous layer washed with hexanes (100 mL). The combined organic layers were dried over sodium sulfate and concentrated by rotary evaporation to give the desired product as a light brown oil (40 g, 195 mmol, 99%). The product was identified by NMR spectroscopy and mass spectrometry and in general was used without further purification. Analytically pure product was obtained by distillation at reduced pressure: by 145-150° C. (0.5 mm).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. temperaturewith cooling by an ice bath
  3. customThe layers were separated
  4. washthe aqueous layer washed with hexanes (100 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-fe821077a8c344a0bd7d9fb7dd04c147
Source dataset
uspto-grants-2014_05
Patent number
US08722574B2

Reaction notes

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