Benzoic Acid → Methyl Benzoate

HRID 1733670Notes

Reaction equation

HRID 1733670 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.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>CO.CCOCC>[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 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of benzoic acid (2.5 g) and triethylamine (5.6 ml) in methanol (5.0 ml) and anhydrous ether (30 ml) is added 1-methanesulfonyloxy-1,2,3-benzotriazole (4.3 g) under cooling. The mixture is stirred for 1 hour and then allowed to stand overnight. The reaction mixture is extracted with ether, and the extract is washed with water, an aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate and then the solvent is distilled off to give methyl benzoate (2.1 g) as an oily substance.

Workup

  1. temperatureunder cooling
  2. waitto stand overnight
  3. extractionThe reaction mixture is extracted with ether
  4. washthe extract is washed with water
  5. dry with materialan aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-94159694000c48c3b701b09e3d4dfc69
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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