Hydrochloric Acid → 4-Phenoxycinnamic acid

HRID 612954Notes

Reaction equation

HRID 612954 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O-:19])(=[O:18])[CH3:17].[K+].Cl>C(OC(=O)C)(=O)C>[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH:17][C:16]([OH:19])=[O:18])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 661394-PhenoxybenzaldehydeHCID 517044Potassium Acetate

Product 1

HCID 209923884-Phenoxycinnamic acidYield 54%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
180 °C

Procedure

4-Phenoxybenzaldehyde (10.0 g) and potassium acetate (9.8 g) were suspended in acetic anhydride (9.5 ml), followed by reflux at 180° C. for 5 hours. After the reaction, the pH of the reaction mixture was adjusted to a value of 2 with hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous NaCl solution, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to obtain the title compound (6.5 g, 54%) as colorless crystals.

Workup

  1. customAfter the reaction
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous NaCl solution
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-bac9b9e64c284b4589bc8fe1cd95a921
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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