Sulfuric Acid → Methyl 3-hydroxy-4-methoxybenzoate

HRID 611465Notes

Reaction equation

HRID 611465 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12575Isovanillic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-hydroxy-4-methoxybenzoic acid (Aldrich, 10 g, 59.5 mmol), methanol (250 ml) and concentrated sulfuric acid (1 ml) was stirred overnight and the product was poured into a mixture of sodium bicarbonate and ice. The aqueous mixture was then extracted three times with ethyl acetate. The resulting organic layers were combined, washed with water and brine, and dried over anhydrous magnesium sulfate. Rotary evaporation of the solution gave 9.5 g of the desired product as a colorless oil. NMR (δ):3.89 (s, 3H), 3.95 (s, 3H).

Workup

  1. extractionThe aqueous mixture was then extracted three times with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRotary evaporation of the solution

Sources & evidence

ORD record
ord-c9ab3beb51f14bf6837ab30eaa5df08a
Source dataset
uspto-grants-1999_12
Patent number
US06001659

Reaction notes

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