Sulfuric Acid → m3OMG

HRID 258152Notes

Reaction equation

HRID 258152 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].S(OC)(O[CH3:18])(=O)=O.[OH-].[Na+].S(=O)(=O)(O)O>>[CH3:18][O:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[CH:9]=[C:4]([CH:3]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6497Dimethyl SulfateHCID 7428Methyl GallateHCID 14798Sodium Hydroxide

Product 1

HCID 99622m3OMGYield 64.5%

Procedure

In 2.95 l of a 5% aqueous solution of borax was dissolved 36.8 g of methyl 3,4,5-trihydroxybenzoate, and the solution was stirred at room temperature for 5 hours. Then, 110.5 ml of dimethyl sulfate and a solution of sodium hydroxide were dropped into the solution and the reaction mixture was further stirred for 5 hours. After cooling, the mixture was made acidic by concentrated sulfuric acid and extracted with ethyl acetate. The solvent was removed from the extract to obtain 25.5 g of methyl 5-methoxy-3,4-dihydroxybenzoate (the yield was 64.5%).

Workup

  1. stirringthe reaction mixture was further stirred for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customThe solvent was removed from the
  5. extractionextract

Sources & evidence

ORD record
ord-f3c66d3fa66b4e9f83bde8816d59fd8d
Source dataset
uspto-grants-1993_11
Patent number
US05264594

Reaction notes

Loading…