Sulfuric Acid → m3OMG

HRID 2120905Notes

Reaction equation

HRID 2120905 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].[OH-].[Na+].[CH3:16]OS(OC)(=O)=O.S(=O)(=O)(O)O>O.C(OCC)(=O)C.CCCCCC>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:16])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

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

Product 1

HCID 99622m3OMGYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl 3,4,5-trihydroxybenzoate(50.0 g, 270 mmol) prepared in Step 1 and borax(54.0 g, 140 mmol) were dissoved in distilled water(1) and the mixture was stirred for 1 hour. To this solution was added sodium hydroxide(13 g, 330 mmol) dissoved in distilled water(100 ml), and the resulting mixture was stirred for 10 minutes. Dimethylsulfate(135 ml, 370 mmol) was added and the mixture was stirred again for 15 hours. The reaction solution was neutralized to pH 7-8 using conc. sulfuric acid, extracted with ethyl acetate and then subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane, 1/2, v/v) to give methyl 3,4-dihydroxy-5-methoxybenzoate(42.5 g, Yield 79%) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred again for 15 hours
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-58c535aa08314ea980b92acf8624b5f4
Source dataset
uspto-grants-2004_02
Patent number
US06693126B2

Reaction notes

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