Benzoic Acid → Methyl Benzoate

HRID 1702163Notes

Reaction equation

HRID 1702163 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11](Cl)(Cl)C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH3:11][O:8][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 11430Potassium CarbonateHCID 11739Methyl trichloroacetate

Product 1

HCID 7150Methyl BenzoateYield 85%

Conditions

Temperature
150 °C

Procedure

A mixture of benzoic acid (1.53 g, 0.0125 mole), methyl trichloroacetate (2.22 g, 0.0125 mole), potassium carbonate (0.035 g) and 18-crown-6 cyclic polyether (0.066 g) was placed in a 25 ml round-bottom flask fitted with a stirrer, distillation head, dry ice receiver and trap. The mixture was heated with stirring to 150° C. Gas evolution was observed to begin at about 90° C. After about 3 hours, the heating was discontinued. The trap contained CHCl3 (approx. 1.5 g). Distillation of the remaining mixture gave methylbenzoate identified by gas-liquid chromatography and nuclear magnetic resonance spectroscopy. Purified yield was 85 percent.

Workup

  1. customwas placed in a 25 ml round-bottom flask
  2. customfitted with a stirrer
  3. distillationdistillation head, dry ice receiver and trap
  4. temperatureThe mixture was heated
  5. customto begin at about 90° C
  6. distillationDistillation of the remaining mixture

Sources & evidence

ORD record
ord-e95963f043b749b4bbb7414519e42b34
Source dataset
uspto-grants-1983_04
Patent number
US04380636

Reaction notes

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