Sulfuric Acid → Methyl 3-hydroxy-4-methoxybenzoate

HRID 611455Notes

Reaction equation

HRID 611455 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-b698703b72c542468a87e7ad1c860696
Source dataset
uspto-grants-1999_12
Patent number
US06001561

Reaction notes

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