Ethanol → 2-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

HRID 612939

Reaction equation

HRID 612939 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH3:14].S(=O)(=O)(O)O>C1C=CC=CC=1>[CH2:13]([O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-

Product 1

HCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Chlorocinnamic acid (300 g) was suspended in benzene (1200 ml), and ethanol (340 g) and conc. sulfuric acid (14 ml) were added thereto, followed by reflux of the resulting mixture for 15 hours. After the reaction mixture had been washed successively with a diluted aqueous NaCl solution (500 ml), a saturated aqueous sodium hydrogencarbonate solution (500 ml) and a dilute aqueous NaCl solution (500 ml), the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was evaporated under reduced pressure to obtain the title compound (334 g, 97%) as a colorless liquid.

Workup

  1. temperatureby reflux of the resulting mixture for 15 hours
  2. washAfter the reaction mixture had been washed successively with a diluted aqueous NaCl solution (500 ml)
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution (500 ml) and a dilute aqueous NaCl solution (500 ml), the organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a941244f89f74b54958785deed1f5d32
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Linked notes

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