Methanol → Methyl 3,5-Dihydroxybenzoate

HRID 2396157Notes

Reaction equation

HRID 2396157 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74243,5-Dihydroxybenzoic Acid

Product 1

HCID 75076Methyl 3,5-DihydroxybenzoateYield 87%

Procedure

A mixture of 3,5-dihydroxybenzoic acid (106 g, 0.69 mol), 1200 ml of methanol and 6 ml of concentrated sulfuric acid is added to a 2L, three-necked round-bottom flask equipped with a Soxhlet extraction apparatus, the thimble of the Soxhlet being packed with 4Å molecular sieves. The solution is stirred and heated at reflux for 24 hours and after removal of the methanol from the reaction solution under reduced pressure, the powder residue is washed with water and recrystallized from water to yield 87 percent of white, needle-like crystals: mp 167°-167.5° C.

Workup

  1. customequipped with a Soxhlet extraction apparatus
  2. temperatureheated
  3. temperatureat reflux for 24 hours
  4. customafter removal of the methanol from the reaction solution under reduced pressure
  5. washthe powder residue is washed with water
  6. customrecrystallized from water
  7. customto yield 87 percent of white, needle-like crystals

Sources & evidence

ORD record
ord-20142fff6a6145ee97ba619cc84ce4b2
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

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