Acetic Acid → 2-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enal

HRID 1395211Notes

Reaction equation

HRID 1395211 reaction equation
[C:1]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[OH-].[K+].[CH:16](=[O:19])[CH2:17][CH3:18].C(O)(=O)C>CO>[C:1]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[C:17]([CH3:18])[CH:16]=[O:19])=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 14797Potassium HydroxideHCID 4737804-(2-Methylbutan-2-yl)benzaldehyde

Product 1

HCID 533951972-Methyl-3-[4-(2-methylbutan-2-yl)phenyl]prop-2-enal

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

162.2 g of p-tert.amyl-benzaldehyde are added under nitrogen gasification to a solution of 1.56 g of potassium hydroxide in 113 ml of methanol and 48.8 g of propionaldehyde are subsequently added dropwise at 40° C. over a period of 6 hours. The mixture is subsequently stirred at 40° C. for an additional hour, 2 ml of acetic acid are added and the mixture is concentrated on a rotary evaporator. The oily suspension is taken up in ether, washed neutral with water, dried and evaporated. By distillation there is obtained pure 3-(p-tert.amyl-phenyl)-2-methyl-acrolein of boiling point 117°-120° C./0.035 Torr.

Workup

  1. additionare subsequently added dropwise at 40° C. over a period of 6 hours
  2. concentrationthe mixture is concentrated on a rotary evaporator
  3. washwashed neutral with water
  4. customdried
  5. customevaporated
  6. distillationBy distillation there

Sources & evidence

ORD record
ord-c926f46e5f784b86b3a6303201b42868
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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