Methanol → methyl 2,4,6-trimethoxybenzoate

HRID 874053Notes

Reaction equation

HRID 874053 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 (CAS #570-02-5) (5.61 g, 26.42 mmol) was suspended in 20 mL of methanol (CAS #67-56-1). Concentrated sulfuric acid (CAS #7664-93-9) (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 (CAS #67-56-1) removed in vacuo. The residues were taken up in 50 mL 5% NaHCO3 (CAS #144-55-8) and extracted with hexane (CAS #110-54-3) until all the solids had dissolved. The hexane extract was dried over anhydrous Na2SO4 (CAS #7757-82-6), filtered, and rotovapped to dryness to give the desired product, methyl 2,4,6-trimethoxybenzoate (CAS #29723-28-2), as a white crystalline solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 24 hrs
  3. customthe methanol (CAS #67-56-1) removed in vacuo
  4. extractionextracted with hexane (CAS #110-54-3) until all the solids
  5. dissolutionhad dissolved
  6. extractionThe hexane extract
  7. dry with materialwas dried over anhydrous Na2SO4 (CAS #7757-82-6)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-575aafe6717a4cd0abca1f378fa7509c
Source dataset
uspto-grants-2015_03
Patent number
US08979260B1

Reaction notes

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