Water → 4-(Octyloxy)-N,N-diphenylaniline

HRID 338040Notes

Reaction equation

HRID 338040 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2[C:18](=[CH:19][CH:20]=[C:21]3[C:26]=2N=CC=C3)[CH:17]=[CH:16][CH:15]=1.[OH2:28].[OH-].[K+].[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:15]([O:28][C:11]1[CH:10]=[CH:9][C:8]([N:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:26]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 13181,10-PhenanthrolineHCID 11487DiphenylamineHCID 14797Potassium Hydroxide

Product 1

HCID 189967534-(Octyloxy)-N,N-diphenylanilineYield 65%

Procedure

Adding diphenylamine (3.36 g, 20 mmol), 1-iodine-4-octyloxy benzene (18.9 g, 98.4 mmol), phenanthroline.H2O (0.2 g), cuprous chloride (0.2 g) and potassium hydroxide (3.36 g, 60 mmol) into toluene (50 mL), mixing at temperature of 100° C. Refluxing for 36 hours and cooling to room temperature, evaporation to eliminate solvent, washing by dilute hydrochloric acid and water for three times, then chloroform extraction. After that, combining organic phase and washing by diluted NaCl solution and water for two times, and then drying by anhydrous magnesium sulfate and filtering, evaporating the solvent, using petroleum ether/dichloromethane (8:1, v/v) as eluent to elutriate the remainder, separating by silica gel column chromatography to obtain a colorless oily liquid, the yield was 65%.

Workup

  1. temperatureRefluxing for 36 hours
  2. customevaporation
  3. washwashing by dilute hydrochloric acid and water for three times
  4. extractionchloroform extraction
  5. washwashing by diluted NaCl solution and water for two times
  6. dry with materialdrying by anhydrous magnesium sulfate
  7. filtrationfiltering
  8. customevaporating the solvent
  9. customseparating by silica gel column chromatography
  10. customto obtain a colorless oily liquid

Sources & evidence

ORD record
ord-4664656a50ac4967af523c2b33fbee88
Source dataset
uspto-grants-2014_11
Patent number
US08889825B2

Reaction notes

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