Hydrochloric Acid → Methyl 5-chloro-3-hydroxythiophene-2-carboxylate

HRID 1200100Notes

Reaction equation

HRID 1200100 reaction equation
Cl[C:2]1([C:8]([O:10][CH3:11])=[O:9])[C:6](=[O:7])[CH:5]=[CH:4][S:3]1.[ClH:12]>C(O)(=O)C>[Cl:12][C:4]1[S:3][C:2]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:7])[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate

Product 1

HCID 54706804Methyl 5-chloro-3-hydroxythiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-chloro-2-methoxycarbonylthiophene-3(2H)-one (30 mmol) in acetic acid (20 ml) was saturated with dry hydrogen chloride gas. After standing for 3 days the solvent was removed under reduced pressure and the oily residue distilled to give a yellow liquid which crystallised on addition of aqueous acetic acid (m.p. 42°-44° C.).

Workup

  1. customthe solvent was removed under reduced pressure
  2. distillationthe oily residue distilled
  3. customto give a yellow liquid which
  4. customcrystallised on addition of aqueous acetic acid (m.p. 42°-44° C.)

Sources & evidence

ORD record
ord-54ac88c49b634371b5a37340dd9d777a
Source dataset
uspto-grants-1990_02
Patent number
US04904686

Reaction notes

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