Acetic Acid → 2-Pentenal, 2-methyl-4-phenyl-

HRID 246985

Reaction equation

HRID 246985 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].[C:5]1([CH:11]([CH3:14])[CH:12]=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].C(O)(=O)C>CO>[CH3:3][C:2](=[CH:12][CH:11]([CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:1]=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 71462-PhenylpropanalHCID 14798Sodium Hydroxide

Product 1

HCID 570411602-Pentenal, 2-methyl-4-phenyl-Yield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

192 g of propionaldehyde are added dropwise to a solution of 402 g of 2-phenylpropan-1-al and 12 g of sodium hydroxide in 1 l of methanol in the course of 6 hours. Stirring is continued for one hour, after which the mixture is neutralized with glacial acetic acid (pH=6), stirred overnight and evaporated down, the residue is taken up with CH2Cl2 /H2O, and the solution is extracted with CH2Cl2. The organic phase is washed with water, dried over Na2SO4, evaporated down again and distilled to give 178 g of 2,4-dimethyl-4-phenylbut-2-en-1-al of boiling point 108°-120° C./0.5 mbar.

Workup

  1. stirringstirred overnight
  2. customevaporated down
  3. extractionthe solution is extracted with CH2Cl2
  4. washThe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated down again
  7. distillationdistilled

Sources & evidence

ORD record
ord-0f72f826f034420aaea23dd9c9ace2bb
Source dataset
uspto-grants-1987_11
Patent number
US04705553

Linked notes

Loading…