Methanol → Benzoic acid, 3,5-dimethyl-, methyl ester

HRID 1449690

Reaction equation

HRID 1449690 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 103563,5-Dimethylbenzoic acid

Product 1

HCID 32786Benzoic acid, 3,5-dimethyl-, methyl esterYield 90%

Procedure

A solution of 3,5-dimethyl benzoic acid (25 g, 0.17 mol) in methanol (250 ml) was treated with sulfuric acid (1 ml, cat. amount) and heated to reflux. After 10 hours, the solution was cooled to room temperature, concentrated to approximately 1/2 volume and poured into 200 ml of crushed ice. The mixture was extracted twice with 200 ml portions of diethyl ether. The organic phase was extracted with saturated aqueous sodium carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting solid was recrystallized from hexanes to yield the product (24.5 g, 90% yield) as volatile white plates. mp=32°-35° C. (lit. mp=35°-36° C.)

Workup

  1. temperatureheated to reflux
  2. concentrationconcentrated to approximately 1/2 volume
  3. additionpoured into 200 ml of crushed ice
  4. extractionThe mixture was extracted twice with 200 ml portions of diethyl ether
  5. extractionThe organic phase was extracted with saturated aqueous sodium carbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was recrystallized from hexanes

Sources & evidence

ORD record
ord-12855e9ebf6145e3baf125f73f8c0817
Source dataset
uspto-grants-1997_02
Patent number
US05599926

Linked notes

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