Methanol → 4-(15-Carboxypentadecylamino)benzaldehyde

HRID 1278392Notes

Reaction equation

HRID 1278392 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 211633224-(15-Carboxypentadecylamino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e85dcacf979a49f3a3ce90ad50b3dd04
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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