Methanol → Methyl 3-chloro-2-methylbenzoate

HRID 1042348Notes

Reaction equation

HRID 1042348 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>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 5077673Methyl 3-chloro-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Approximately two drops of sulfuric acid were added to a solution of 3-chloro-2-methyl-benzoic acid (5.00 g, 29.30 mmol) in methanol and the resulting reaction mixture was refluxed for 14 hours. The reaction mixture was cooled to room temperature, and concentrated, then diluted with EtOAc. The organic layer was washed with saturated NaHCO3 (3×150 mL), H2O (2×250 mL), brine (1×250 mL) and dried over MgSO4. The crude product was purified by column chromatography using hex:EtOAc (4.5:0.5) as the eluant to give the title ester. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 2.60 (s, 3H), 3.90 (s, 3H), 7.16 (t, J=7.325 Hz, 1H), 7.49 (d, J=7.91 Hz, 1H), 7.69 (d, J=7.91 Hz, 1H).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 14 hours
  3. concentrationconcentrated
  4. additiondiluted with EtOAc
  5. washThe organic layer was washed with saturated NaHCO3 (3×150 mL), H2O (2×250 mL), brine (1×250 mL)
  6. dry with materialdried over MgSO4
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-746d95bfd1154ce4abd4511339abb83d
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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