Methanol → Benzoic acid, 3-methyl-, methyl ester

HRID 1867214Notes

Reaction equation

HRID 1867214 reaction equation
C[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[CH3:17]O>>[C:3]1([CH3:11])[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:17])=[O:9])[CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 117822,3-Dimethylbenzoic acid

Product 1

HCID 7435Benzoic acid, 3-methyl-, methyl ester

Conditions

Temperature
65 °C

Procedure

A 3 L reaction flask was charged with methyl m-toluic acid (0.5 kg), anhydrous methanol (2 L), and sulfuric acid (100 g). The mixture was heated to reflux (65° C.) and aged for 14-20 hours, then cooled to an ambient temperature, and the acid was quenched with a two molar equivalent of sodium acetate. Methanol was distilled out of the flask and the mixture was washed with 1 L brine. The crude product was vacuum distilled to give 480 g of methyl m-toluate, which had a boiling point of 113° C. at a pressure of 25 mmHg.

Workup

  1. customA 3 L reaction flask
  2. temperatureThe mixture was heated
  3. temperaturecooled to an ambient temperature
  4. customthe acid was quenched with a two molar equivalent of sodium acetate
  5. distillationMethanol was distilled out of the flask
  6. washthe mixture was washed with 1 L brine
  7. distillationdistilled

Sources & evidence

ORD record
ord-a506c091c4f04381ae675bd16075ec70
Source dataset
uspto-grants-2009_12
Patent number
US07632792B2

Reaction notes

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