Methanol → methyl 2,4,6-trimethoxybenzoate

HRID 516796Notes

Reaction equation

HRID 516796 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[C:4]=1[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:15][O:14][C:8]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([O:7][CH3:21])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 684412,4,6-Trimethoxybenzoic acid

Product 1

HCID 289740methyl 2,4,6-trimethoxybenzoate

Procedure

2,4,6-trimethoxybenzoic acid (5.61 g, 26.42 mmol) was suspended in 20 mL of methanol. Concentrated sulfuric acid (1 mL) was added to the mixture, and the reaction heated to reflux for 24 hrs. The reaction was cooled to room temperature, and the methanol removed in vacuo. The residues were taken up in 50 mL 5% NaHCO3 and extracted with hexane until all the solids had dissolved. The hexane extract was dried over anhydrous Na2SO4, filtered, and the volatiles were removed in a rotary evaporator to dryness to give the desired product, methyl 2,4,6-trimethoxybenzoate, as a white crystalline solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 24 hrs
  3. customthe methanol removed in vacuo
  4. extractionextracted with hexane until all the solids
  5. dissolutionhad dissolved
  6. extractionThe hexane extract
  7. dry with materialwas dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customthe volatiles were removed in a rotary evaporator to dryness

Sources & evidence

ORD record
ord-365bf7d813b04b9db6dca205c8380df6
Source dataset
uspto-grants-2015_08
Patent number
US09115066B2

Reaction notes

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