2,3-Dihydroxybenzoic Acid → Methyl 2,3-Dihydroxybenzoate

HRID 1784096Notes

Reaction equation

HRID 1784096 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>S(=O)(=O)(O)O>[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 192,3-Dihydroxybenzoic AcidHCID 887Methanol

Product 1

HCID 75484Methyl 2,3-Dihydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 2,3-dihydroxybenzoic acid (5 g), methanol (50 ml) and concentrated sulphuric acid (10 drops) was stirred and heated to 60° C. for 24 hours. The mixture was evaporated and the residue was taken up in ethyl acetate. The organic solution was washed with a saturated solution of sodium bicarbonate, dried over magnesium sulphate and evaporated to give methyl 2,3-dihydroxybenzoate (2.19 g); NMR Spectrum: (CDCl3) 3.95 (s, 3H), 5.7 (s, 1H), 6.8 (t, 1H), 7.15 (d, H), 7.35 (d, H).

Workup

  1. customThe mixture was evaporated
  2. washThe organic solution was washed with a saturated solution of sodium bicarbonate
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-a45a50c6621a4e088906e4c8c0cd3295
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

Loading…