Acetic Acid → m-Ethylbenzaldehyde

HRID 1919804Notes

Reaction equation

HRID 1919804 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#N)[CH3:12].C(O)(=[O:23])C.O>C1(C)C=CC=CC=1>[CH2:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:23])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 96692Benzonitrile, 3-ethyl-HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 118623m-EthylbenzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Add a 1 M solution of diisobutylaluminum hydride in toluene (76 mmol) dropwise to a solution of m-ethylbenzonitrile (38 mmol) in toluene (50 mL) under nitrogen in a dry ice-acetone bath. Stir for 30 minutes then add acetic acid (20 mL) dropwise followed by water (100 mL). Stir the reaction for 2 hours. Separate the layers and extract the aqueous with toluene. Dry the combined organic layers over sodium sulfate, and evaporate to give the title compound (4.5 g, 88% yield). 1HNMR (400.43 MHz, CDCl3): δ 9.97 (s, 1H), 7.69-7.66 (m, 2H), 7.46-7.40 (m, 2H), 2.71 (q, J=7.6 Hz, 2H), 1.25 (t, J=7.5 Hz, 3H).

Workup

  1. stirringStir
  2. customthe reaction for 2 hours
  3. customSeparate the layers
  4. extractionextract the aqueous with toluene
  5. dry with materialDry the combined organic layers over sodium sulfate
  6. customevaporate

Sources & evidence

ORD record
ord-051d9be3052b4487a2e752453cd9c485
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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