Acetic Acid → 2-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl-

HRID 1733271

Reaction equation

HRID 1733271 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH:15](=[O:18])[CH2:16][CH3:17].C(O)(=O)C>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:16]([CH3:17])[CH:15]=[O:18])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 14797Potassium HydroxideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 1146592-Propenal, 3-[4-(1,1-dimethylethyl)phenyl]-2-methyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

108.5 g of p-tert.butyl-benzaldehyde are added under nitrogen gasification to a solution of 1.4 g of potassium hydroxide in 100 ml of methanol and 39.2 g of propionaldehyde are subsequently added dropwise at 40° C. over a period of 6 hours. Subsequently, the mixture is further stirred at 40° C. for 1 hour, 1.5 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.butyl-phenyl)-2-methyl-acrolein of boiling point 165° C./11 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-7ba3d7c254654ce5a4ed8c6e78790a40
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Linked notes

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