Acetic Acid → HCID 367965, compound

HRID 2286529Notes

Reaction equation

HRID 2286529 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[OH-].[K+].[CH:12](=[O:15])[CH2:13][CH3:14].C(O)(=O)C>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:13]([CH3:14])[CH:12]=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 14797Potassium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 367965HCID 367965, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 124 g (1 mole) of 4-fluorobenzaldehyde and 8 g (0.143 mole) of potassium hydroxide in 500 ml ethanol at room temperature was added dropwise a solution of 52.2 g (0.9 mole) of propionaldehyde in 100 ml ethanol. After stirring for 0.5 hour, the mixture was acidified with acetic acid and concentrated by rotary evaporation. The residue was partitioned between methylene chloride and water. The aqueous layer was extracted three times with additional methylene chloride. The combined organic layers were dried and concentrated. Distillation through a 12-inch vacuum jacketed column gave 113.5 g (77%) of pale yellow low-melting crystalline product, b.p. 70°-72° C. (0.4-0.7 mm).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customThe residue was partitioned between methylene chloride and water
  3. extractionThe aqueous layer was extracted three times with additional methylene chloride
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. distillationDistillation through a 12-inch vacuum

Sources & evidence

ORD record
ord-1660676866b94bc5acc71efe6f3d27ac
Source dataset
uspto-grants-1981_05
Patent number
US04267190

Reaction notes

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