Benzoic Acid → Methyl Benzoate

HRID 1058175Notes

Reaction equation

HRID 1058175 reaction equation
[CH2:1]1CCN2C(=NCCC2)CC1.[C:12]([OH:20])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.O>[C:12]([O:20][CH3:1])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

DBU (2.5 g, 16.4 mmol) was added to a mixture of benzoic acid (2.0 g, 16.4 mmol) in DMC (20 mL) and the resulting mixture was heated to reflux (90° C.) for 2.5 hours. The reaction mixture was cooled to ambient temperature and diluted with CH2Cl2 (50 mL) and water (40 mL). The organic layer was separated and washed in sequence with 2 M HCl (2×40 mL), saturated aqueous NaHCO3 (40 mL) and water (2×40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl benzoate as an oil. The yield of the methyl benzoate as determined by HPLC was 97-98% conversion.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customThe organic layer was separated
  4. washwashed in sequence with 2 M HCl (2×40 mL), saturated aqueous NaHCO3 (40 mL) and water (2×40 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5e239449ed504f23a649cf98c84ceb5f
Source dataset
uspto-grants-2003_02
Patent number
US06515167B1

Reaction notes

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