Sulfuric Acid → Methyl Vanillate

HRID 1911914Notes

Reaction equation

HRID 1911914 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].S(=O)(=O)(O)O.[C:18]([O-])(O)=O.[Na+]>CO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8468Vanillic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 19844Methyl VanillateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-3-methoxybenzoic acid (0.1 g, 0.59 mmol) in 10 mL of methanol was added 0.3 mL of conc. sulfuric acid, and refluxed overnight. The pH of the solution was shifted into an alkaline zone by addition of 5% aqueous NaHCO3 solution. Following extraction with EtOAc, the extract was washed with a saturated NaCl aqueous solution. It was dried over MgSO4 and the solvent was removed by concentration under reduced pressure to afford the compound 9 (0.107 g, 98%).

Workup

  1. temperaturerefluxed overnight
  2. extractionextraction with EtOAc
  3. washthe extract was washed with a saturated NaCl aqueous solution
  4. dry with materialIt was dried over MgSO4
  5. customthe solvent was removed by concentration under reduced pressure

Sources & evidence

ORD record
ord-c9d7f7da50f745ba864b6f1f9d0ee5f2
Source dataset
uspto-grants-2013_12
Patent number
US08604214B2

Reaction notes

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