Sulfuric Acid → m3OMG

HRID 1964208Notes

Reaction equation

HRID 1964208 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([OH:11])=[C:6]([OH:12])[CH:5]=1.[CH3:14]OS(OC)(=O)=O.[OH-].[Na+].OS(O)(=O)=O>O>[OH:12][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH3:14])[C:7]=1[OH:11])[C:3]([O:2][CH3:1])=[O:13]

Participants

6

Reactant 4

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

Product 1

HCID 99622m3OMGYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3,4,5-trihydroxy-benzoic acid methyl ester (50 g, 0.27 mol) and Na2B4O7 (50 g) in water (1000 mL) was added Me2SO4(120 mL) and aqueous NaOH solution (25%, 200 mL) successively at room temperature. The mixture was stirred at room temperature for 6 h before it was cooled to 0° C. The mixture was acidified to pH ˜2 by adding conc. H2SO4 and then filtered. The filtrate was extracted with EtOAc (500 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give methyl 3,4-dihydroxy-5-methoxybenzoate (15.3 g 47%), which was used in the next step without further purification.

Workup

  1. temperaturewas cooled to 0° C
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc (500 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c9fa8c4084c4780baba3c768d045c94
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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