Hydrochloric Acid → Methyl Vanillate

HRID 19989

Reaction equation

HRID 19989 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].Cl.[CH3:14]O>>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8468Vanillic Acid

Product 1

HCID 19844Methyl VanillateYield 91.5%

Procedure

A solution of 4-hydroxy-3methoxy benzoic acid (7.2 g) in methanol (150 ml) was refluxed in presence of concentrated hydrochloric acid (0.5 ml) for 12 hrs. After concentrating under reduced pressure, the residue was dissolved in ethyl acetate (200 ml) and washed with water (50 ml) 10% sodium bicarbonate solution (2×50 ml), water (50 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 7.25 g of 4-hydroxy-3-methoxy benzoic acid methyl ester. (Yield=91.5%).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
  3. washwashed with water (50 ml) 10% sodium bicarbonate solution (2×50 ml), water (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-05457a0b469b492b972192d9954573fb
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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