Methanol → Methyl Gentisate

HRID 374441Notes

Reaction equation

HRID 374441 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 34692,5-Dihydroxybenzoic acid

Product 1

HCID 75077Methyl Gentisate

Conditions

Temperature
70 °C

Procedure

A solution of 50 g (0.32 mole) of 2,5-dihydroxybenzoic acid in 260 ml of methanol, at 0° C., was combined with 33 ml of sulphuric acid. The resulting solution was heated to 70° C. under stirring. After 6 hours the reaction mixture was cooled to room temperature and concentrated to small volume under vacuum. The resulting oily layer was taken up with sodium hydroxyde 5N and extracted with ethyl acetate the organic layer was washed with water, dried over sodium sulphate and evaporated under vacuum, to provide 52 g of methyl 2,5-dihydroxybenzoate which were used in the next step as obtained.

Workup

  1. customat 0° C.
  2. temperatureAfter 6 hours the reaction mixture was cooled to room temperature
  3. concentrationconcentrated to small volume under vacuum
  4. extractionextracted with ethyl acetate the organic layer
  5. washwas washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-f0d67b1b150a4f1f860145ae64b953a6
Source dataset
uspto-grants-1996_01
Patent number
US05480882

Reaction notes

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