Methanol → Methyl 2,6-dihydroxybenzoate

HRID 978075

Reaction equation

HRID 978075 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>>[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:8]=1[C:9]([O:11][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 93382,6-Dihydroxybenzoic Acid

Product 1

HCID 519869Methyl 2,6-dihydroxybenzoate

Procedure

Concentrated sulfuric acid (40 ml) was carefully added to a solution of 2,6-dihydroxybenzoic acid (133 g, 0.86 mol) in absolute methanol (500 ml). The reaction mixture was heated at reflux temperature for 24 hours, cooled, and evaporated. The residue was added to aa saturated sodium hydrogencarbonate solution, and the resulting solid was collected by filtration, washed with water, and dried in vacuo over phosphorus peroxide; yield 49 g (34%). NMR (CDCl3, 60 MHz): δ4.02 (s, CO2CH3) p.p.m.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 24 hours
  3. temperaturecooled
  4. customevaporated
  5. additionThe residue was added to aa saturated sodium hydrogencarbonate solution
  6. filtrationthe resulting solid was collected by filtration
  7. washwashed with water
  8. dry with materialdried in vacuo over phosphorus peroxide

Sources & evidence

ORD record
ord-5dfcbdd2d0b24f68831320d9c4da059c
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Linked notes

Loading…