Methanol → Methyl 3-chloro-2-methylbenzoate

HRID 1870507Notes

Reaction equation

HRID 1870507 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 5077673Methyl 3-chloro-2-methylbenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 3-chloro-2-methylbenzoic acid (1.00 g, 5.86 mmol) in methanol (25 mL) was added 3 drops of sulfuric acid. The mixture was stirred at reflux for 18 h. After concentrating the residue was dissolved in ether, washed with 10% sodium hydroxide solution, brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 0.95 g (88%) of the title compound as a white solid: 1H NMR (250 MHz, CDCl3) d 7.62 (d, 1 H), 7.41 (d, 1 H), 7.05 (t, 1 H), 3.82 (s, 3 H), 2.55 (s, 3 H).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationAfter concentrating the residue
  3. dissolutionwas dissolved in ether
  4. washwashed with 10% sodium hydroxide solution, brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-91cab95d54ad41349e115fd515500bc5
Source dataset
uspto-grants-2000_08
Patent number
US06096897

Reaction notes

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