Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 253266Notes

Reaction equation

HRID 253266 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12575Isovanillic Acid

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoateYield 100%

Procedure

To a suspension of 3-hydroxy-4-(methyloxy)benzoic acid (25 g, 149 mmol.) in methanol (200 mL) was added concentrated sulfuric acid (1 mL) and the mixture was brought to reflux over 18 hours. The resulting homogeneous solution was cooled to room temperature, concentrated in vacuo and the residual oil taken into ethyl acetate (300 mL). The solution was washed once with water, saturated aqueous sodium hydrogencarbonate then brine and dried over anhydrous magnesium sulfate. Filtration and concentration gave methyl 3-hydroxy-4-(methyloxy)benzoate (27 g, 100% yield) as an oil. 1H NMR (400 MHz, CDCl3): 7.59 (dd, 1H), 7.57 (d, 1H), 6.85 (d, 1H), 5.72 (s, 1H), 3.93 (s, 3H), 3.87 (s, 3H).

Workup

  1. temperatureto reflux over 18 hours
  2. concentrationconcentrated in vacuo
  3. washThe solution was washed once with water, saturated aqueous sodium hydrogencarbonate
  4. dry with materialbrine and dried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1644616bda074dc38c3b442a22c41c54
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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