Methanol → Methyl 4-methoxy-2-methylbenzoate

HRID 1761005Notes

Reaction equation

HRID 1761005 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(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][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 1118Sulfuric AcidHCID 5972164-Methoxy-2-methylbenzoic acid

Product 1

HCID 13257269Methyl 4-methoxy-2-methylbenzoateYield 98%

Procedure

According to J. Org. Chem. 33:494 (1968), a mixture of 4-methoxy-2-methylbenzoic acid (20 g, 120 mmol) and MeOH (97 mL) containing sulfuric acid (conc., 0.6 mL) was heated under reflux 48 h. After cooling the mixture was evaporated and the residue diluted with diethyl ether and washed with a saturated sodium hydrogen carbonate solution and brine. The organic phase was then separated and dried over sodium sulphate. After evaporation the residue was distilled through a 8 cm Vigreux column to afford the title compound (21.2 g, 98%) as a colourless liquid. Bp 60° C./1 mbar. MS: m/e=180.3 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux 48 h
  3. temperatureAfter cooling the mixture
  4. customwas evaporated
  5. additionthe residue diluted with diethyl ether
  6. washwashed with a saturated sodium hydrogen carbonate solution and brine
  7. customThe organic phase was then separated
  8. dry with materialdried over sodium sulphate
  9. customAfter evaporation the residue
  10. distillationwas distilled through a 8 cm Vigreux column

Sources & evidence

ORD record
ord-2963320e9fd249a2811d6dd15ed09052
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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