Methanol → HCID 13019276, compound

HRID 1105698Notes

Reaction equation

HRID 1105698 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([NH:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#N)=[CH:30][CH:29]=1)[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][CH3:26].C[OH:37]>C1(C)C=CC=CC=1.ClCCl>[CH2:11]([NH:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:37])=[CH:30][CH:29]=1)[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][CH3:26]

Participants

6

Reactant 3

HCID 887MethanolHCID 13019275HCID 13019275, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13019276HCID 13019276, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Di-isobutylaluminum hydride (54-ml., 25% solution in toluene) is added with stirring to a solution of p-hexadecylaminobenzonitrile (11.4 g.) 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. The crude product is dissolved in dichloromethane and filtered through hydrated magnesium silicate (80 g.) to give a white crystalline material on removal of the solvent. The product is recrystallized from dichloromethane/hexanes giving colorless fine needles (6.0 g.), m.p. 84°-85° C.

Workup

  1. additionThe temperature rises to 40° C. during the addition which
  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. filtrationfiltered through hydrated magnesium silicate (80 g.)
  12. customto give a white crystalline material
  13. customon removal of the solvent
  14. customThe product is recrystallized from dichloromethane/hexanes giving colorless fine needles (6.0 g.), m.p. 84°-85° C.

Sources & evidence

ORD record
ord-2d0c0228bbbe45969f3b3ddba15097a4
Source dataset
uspto-grants-1982_01
Patent number
US04309553

Reaction notes

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