Methanol → Methyl 4-hydroxythiophene-2-carboxylate

HRID 655642Notes

Reaction equation

HRID 655642 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-f28e690200c64e3e83fa2728ce404274
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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