Methanol → Methyl 4-hydroxythiophene-2-carboxylate

HRID 1907366Notes

Reaction equation

HRID 1907366 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[S:9][CH:10]=1.[CH3:14]O>>[OH:5][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[S:9][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 132779074-Hydroxythiophene-2-carboxylic acid

Product 1

HCID 13277908Methyl 4-hydroxythiophene-2-carboxylate

Procedure

Thionyl chloride (1.6 ml) was added dropwise to a methanol solution (20 ml) of 4-hydroxythiophene-2-carboxylic acid (1.1 g, 7.6 mmol) under ice cooling. The solution mixture was refluxed with heating for 5 hours. The reaction solution was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) and concentrated/dried under reduced pressure to obtain methyl 4-hydroxythiophene-2-carboxylate (0.7 g) as white powder.

Workup

  1. temperatureThe solution mixture was refluxed
  2. temperaturewith heating for 5 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extraction solution with ethyl acetate was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
  7. customconcentrated/dried under reduced pressure

Sources & evidence

ORD record
ord-ced317196d414c2fb17a3d74f0497f09
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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