Methanol → Methyl 3,5-Dihydroxybenzoate

HRID 1917586Notes

Reaction equation

HRID 1917586 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].[CH3:12]O>OS(O)(=O)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 74243,5-Dihydroxybenzoic Acid

Product 1

HCID 75076Methyl 3,5-DihydroxybenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3,5-dihydroxybenzoic acid (20.0 g, 129.9 mmol) in dry methanol (100 mL) and H2SO4 (1 mL) was refluxed for 20 h. The volatile product was removed in vacuo and the residue was redissolved in ethyl acetate (EA) and washed with aqueous NaHCO3, water and brine. The organic phase was dried with anhydrous sodium sulphate and the solvent was evaporated to yield methyl 3,5-dihydroxybenzoate as a white colored solid (95% yield, m.p.=170° C.). 1H-NMR (300 MHz, CDCl3) δ 7.1 (d, 2H), 6.6 (t, 1H), 4.9 (s, OH), 3.9 (s, OCH3).

Workup

  1. customThe volatile product was removed in vacuo
  2. dissolutionthe residue was redissolved in ethyl acetate (EA)
  3. washwashed with aqueous NaHCO3, water and brine
  4. dry with materialThe organic phase was dried with anhydrous sodium sulphate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-12185de996e54c3bac859a1670cf1130
Source dataset
uspto-grants-2013_12
Patent number
US08618298B2

Reaction notes

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