Sulfuric Acid → 2,6-Diethylbenzaldehyde

HRID 920570Notes

Reaction equation

HRID 920570 reaction equation
C(N=[CH:6][C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:15][CH3:16])CCC.[OH:17]S(O)(=O)=O>O.CCOC(C)=O>[CH2:15]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][CH3:14])[C:7]=1[CH:6]=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 66652926Butyl-(2,6-diethyl-benzylidene)-amine

Product 1

HCID 131847782,6-DiethylbenzaldehydeYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of butyl-(2,6-diethyl-benzylidene)-amine (1.10 g; 5.06 mmol) in water (20 mL) was added H2SO4 (5.00 ml; 93.80 mmol), and the resulting mixture was heated under reflux for 2 hours. After cooling to RT the mixture was diluted with EtOAc, and washed with water, a 5% aqueous NaHCO3-solution and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 2,6-diethyl-benzaldehyde (0.72 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c766c47d4ca246eb994408904eefbf76
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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