Hydrochloric Acid → 2-Methyl-5-phenylbenzaldehyde

HRID 1883617Notes

Reaction equation

HRID 1883617 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[C:4]#N.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=[O:28])C.Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 111715372-Methyl-5-phenylbenzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 120565292-Methyl-5-phenylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under nitrogen atmosphere, 126 g (650 mmol) of 2-methyl-5-phenylbenzonitrile was dissolved in 700 ml of anhydrous toluene, and to the resulted solution was dropped 780 ml of a toluene solution of diisobutyl aluminum hydride (1.0 M solution; 780 mmol) at −10 to 0° C., and the mixture was stirred at room temperature overnight. To the reaction solution was dropped 25 ml of ethyl acetate, and this was poured into a mixture of 2.5 L of ice water and 270 ml of concentrated hydrochloric acid. After stirring at 70 to 75° C. for 1 hour, the mixture was cooled to room temperature, and separated. The organic layer was washed with water, saturated sodium bicarbonate solution, then, water, and concentrated to obtain 123 g of 2-methyl-5-phenylbenzaldehyde.

Workup

  1. stirringAfter stirring at 70 to 75° C. for 1 hour
  2. temperaturethe mixture was cooled to room temperature
  3. customseparated
  4. washThe organic layer was washed with water, saturated sodium bicarbonate solution
  5. concentrationwater, and concentrated

Sources & evidence

ORD record
ord-195148abef4c4227b3dcd6963898ee70
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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