Sulfuryl chloride → Methyl 4-hydroxythiophene-3-carboxylate

HRID 1732929Notes

Reaction equation

HRID 1732929 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([OH:10])[CH2:7][S:8][CH:9]=1)=[O:4].S(Cl)(Cl)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:10])=[CH:7][S:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 54177579HCID 54177579, compound

Product 1

HCID 12520007Methyl 4-hydroxythiophene-3-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

80 Parts of 3-hydroxy-dihydrothiophene-4-carboxylic acid methyl ester are dissolved in 800 parts by volume of methylene chloride. 74.3 parts of sulfuryl chloride in 200 parts by volume of methylene chloride are added in the course of one hour at from 10° to 15° C., whilst passing nitrogen into the mixture. The mixture is then stirred for 30 minutes at from 10° to 15° C., after which it is extracted by shaking with 500 parts of water and 300 parts by volume of a 5 percent strength by weight sodium bicarbonate solution. The organic phase is dried and evaporated. The residue is distilled. 60.5 parts (77% of theory) of 3-hydroxy-thiophene-4-carboxylic acid methyl ester of boiling point 76°-84° C./0.07-0.1 mbar are obtained.

Workup

  1. extractionafter which it is extracted
  2. stirringby shaking with 500 parts of water and 300 parts by volume of a 5 percent strength by weight sodium bicarbonate solution
  3. customThe organic phase is dried
  4. customevaporated
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-007819e0b5fd4ddd852ddc779e7f7883
Source dataset
uspto-grants-1980_12
Patent number
US04239897

Reaction notes

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