Hydrochloric Acid → 2-Methylthiophene-3-carboxylic acid

HRID 644802

Reaction equation

HRID 644802 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl>C(O)C.O>[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10464736Ethyl 2-methylthiophene-3-carboxylate

Product 1

HCID 46254092-Methylthiophene-3-carboxylic acidYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-methyl-3-thiophenecarboxylate (3.42 g, 20.09 mmol; see step (ii) above) was dissolved in ethanol (5 mL) to which was added a solution of sodium hydroxide (3.2145 mg, 80.362 mmol) in water (10 mL). The reaction mixture was heated under reflux for 2 h. The volume was reduced to half under reduced pressure at 40° C. and the residue was cooled with ice water. Dilute HCl was added dropwise with stirring until pH 2. The white solid material was filtered off, washed with water and dried under reduced pressure at 50° C. to give the required material (2.1850 mg, 77% yield), m.p. 115-117° C., lit. m.p. 116-117° C. (see D. W. Knight, A. P. Nott J. Chem. Soc., Perkin Trans. 1 791-794 (1983)).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. customwas reduced to half under reduced pressure at 40° C.
  4. filtrationThe white solid material was filtered off
  5. washwashed with water
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-f49607a9e93249daaab070e2dcce2746
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Linked notes

Loading…