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

HRID 338040ノート

反応式

HRID 338040 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

HCID 189967534-(Octyloxy)-N,N-diphenylaniline収率 65%

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-4664656a50ac4967af523c2b33fbee88
出典データセット
uspto-grants-2014_11
特許番号
US08889825B2

反応ノート

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