Methanol → 4-(15-Carboxypentadecylamino)benzaldehyde

HRID 904247ノート

反応式

HRID 904247 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#N)=[CH:32][CH:31]=1)([OH:13])=[O:12].C[OH:39]>C1(C)C=CC=CC=1>[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:39])=[CH:32][CH:31]=1)([OH:13])=[O:12]

参加物

5

反応物 3

HCID 887MethanolHCID 211633634-(15-Carboxypentadecylamino)benzonitrileHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 211633224-(15-Carboxypentadecylamino)benzaldehyde

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Di-iso-butylaluminum hydride (54 ml., 25% solution in toluene) is added with stirring to a solution of 5.1 g. of 4-(15-carboxypentadecylamino)benzonitrile under a nitrogen atmosphere. The temperature rises to 40° C. during the addition which takes 30 minutes and the reaction is then stirred for 1 hour. A solution of methanol in toluene (50 ml., 1:1) is added over 30 minutes and the mixture is poured into vigorously stirred ice-cold aqueous sulfuric acid (500 ml., 5%). After 10 minutes diatomaceous earth (30 g.) is added, the mixture filtered and the organic layer separated. The aqueous solution is extracted twice with toluene (100 ml.) and the combined organic layers are washed with aqueous sodium bicarbonate, dried over magnesium sulfate, decolorized with charcoal, filtered and evaporated in vacuo to give a light yellow crystalline solid. Recrystallization from hexane affords 4-(15-carboxypentadecylamino)benzaldehyde as a white solid.

後処理

  1. additionThe temperature rises to 40° C. during the addition which
  2. stirringthe reaction is then stirred for 1 hour
  3. additionAfter 10 minutes diatomaceous earth (30 g.) is added
  4. filtrationthe mixture filtered
  5. customthe organic layer separated
  6. extractionThe aqueous solution is extracted twice with toluene (100 ml.)
  7. washthe combined organic layers are washed with aqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto give a light yellow crystalline solid
  12. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-61b8df7eb5ef44dda47e58c94967a24b
出典データセット
uspto-grants-1980_10
特許番号
US04230628

反応ノート

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