Benzoic Acid → Methyl Benzoate

HRID 1733674Notes

Reaction equation

HRID 1733674 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](N(CC)CC)C.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=O)=CC=1.CO>C(Cl)(Cl)Cl>[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 887MethanolHCID 8471Triethylamine2×HCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzoic acid (1.22 g) and triethylamine (1.4 ml) in chloroform (15 ml) is added 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (3.44 g) and the mixture is allowed to stand for 1.5 hours. To the mixture are added methanol (1.6 ml) and triethylamine (1.4 ml), whereby exothermic reaction occurrs. After reacting them for 1 hour and 20 minutes, chloroform is distilled off and to the resulting residue are added water and ether. The ether layer is washed with water, an aqueous sodium hydrogen carbonate and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give methyl benzoate (1.26 g).

Workup

  1. additionTo the mixture are added
  2. customfor 1 hour
  3. distillation20 minutes, chloroform is distilled off and to the resulting residue
  4. additionare added water and ether
  5. washThe ether layer is washed with water
  6. dry with materialan aqueous sodium hydrogen carbonate and water in order and dried over anhydrous magnesium sulfate
  7. customAfter drying
  8. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-32aed759dddb4ef18f76729624f5fb97
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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