Diethyl Ether → 4-Phenylbutanal

HRID 354581Notes

Reaction equation

HRID 354581 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.CC[O:24]CC>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74897BenzenebutanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 290304-Phenylbutanal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 4-phenylbutyronitrile (21.7 g, 0.12 mole) in ether (400 ml) at 78° C. is added 85 ml. of 25.3% diisobutylaluminum hydride in toluene over a period of 1 hour. After an additional 1 hour, the dry ice-acetone bath is removed and the reaction mixture is stirred at ambient temperature for 3 hours. The reaction mixture is added slowly to 5% aqueous sulfuric acid and then is extracted with several portions of ether. The ether extracts are combined, washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. After removal of the ether, the residual yellow oil is distilled in vacuo to give an oil.

Workup

  1. additionis added 85 ml
  2. customthe dry ice-acetone bath is removed
  3. additionThe reaction mixture is added slowly to 5% aqueous sulfuric acid
  4. extractionis extracted with several portions of ether
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the ether
  8. distillationthe residual yellow oil is distilled in vacuo
  9. customto give an oil

Sources & evidence

ORD record
ord-1ecd178d48b140dd8a52050c016d8730
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Reaction notes

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