Methanol → Methyl 3-hydroxy-5-methoxybenzoate

HRID 881971Notes

Reaction equation

HRID 881971 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].OS(O)(=O)=O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Procedure

To a stirred solution of methyl 3,5-dihydroxybenzoate (80 g, 0.52 mol) in CH3OH (600 ml), was added concentrated H2SO4 (40 ml) in portions at room temperature. The reaction mixture was heated to reflux temperature for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed with a saturated aqueous Na2CO3 solution, brine, dried over Na2SO4 and concentrated under reduced pressure to give methyl 3-hydroxy-5-methoxybenzoate (73 g) as a white solid. The crude product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 4 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed with a saturated aqueous Na2CO3 solution, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c28b1af07c54891afabb8d25c0ccb57
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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