Methanol → HCID 20482571, compound

HRID 648307Notes

Reaction equation

HRID 648307 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][CH2:12][CH2:13][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][NH:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#N)=[CH:31][CH:30]=1.C[OH:38]>C1(C)C=CC=CC=1>[Br:11][CH2:12][CH2:13][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][NH:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:38])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 20482580HCID 20482580, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20482571HCID 20482571, compound

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 4-(16-bromohexadecylamino)benzonitrile (11.4 g.) under a nitrogen atmosphere. The temperature rises to 40° C. during the 30 minute addition and then the reaction is then stirred for 1 hour. A solution of methanol in toluene (50 ml., 1:1) was added over 30 minutes and the mixture is poured into vigorously stirred ice-cold aqueous sulfuric acid (50 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. The crude product is recrystallized from dichloromethane-hexane to yield 4-(16-bromohexadecylamino)benzaldehyde as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6eaab0017e0046baa57e5bd751e6bb0c
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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