Methanol → Methyl 4-methoxy-2-methylbenzoate

HRID 2261784Notes

Reaction equation

HRID 2261784 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1.S(Cl)(Cl)=O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 5972164-Methoxy-2-methylbenzoic acid

Product 1

HCID 13257269Methyl 4-methoxy-2-methylbenzoateYield 81%

Procedure

To an ambient temperature suspension of 4-Methoxy-2-methyl-benzoic acid (1.0 g, 6.02 mmol) in MeOH (10 mL) is added thionyl chloride (1.10 mL, 15.04 mmol) dropwise. The reaction mixture is heated to reflux. After 3 h, the reaction is concentrated and the residue is partitioned between EtOAc and NaHCO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated to yield the title compound (877 mg, 81%) 1H NMR (400 MHz, CDCl3) δ 7.95-7.91 (m, 1H), 6.77-6.72 (m, 2H), 3.86 (s, 3H), 3.84 (s, 3H).

Workup

  1. temperatureThe reaction mixture is heated to reflux
  2. concentrationthe reaction is concentrated
  3. customthe residue is partitioned between EtOAc and NaHCO3
  4. extractionThe aqueous layer is extracted with EtOAc
  5. washthe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7e1c831566654d02b8d22b8fede5c1ac
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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