Sodium Hydroxide → 49814-46-2

HRID 869460Notes

Reaction equation

HRID 869460 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([O:10]CC)=[O:9])=[C:4]([CH3:7])[S:5][CH:6]=1.[OH-].[Na+]>CCO>[Cl:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[C:4]([CH3:7])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71226916HCID 71226916, compound

Product 1

HCID 2336185449814-46-2

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 4-chloro-2-methylthiophene-3-carboxylate (F-6) (4.98 g, 24.3 mmol, 1.0 eq) in EtOH (50 mL) ar RT, aqueous NaOH solution (20%, 14.6 g, 73.0 mmol, 3.0 eq) is added and the resulting mixture is stirred at reflux for 1 h. The mixture is allowed to cool to RT and concentrated in vacuo. The residue is poured into ice water (30 mL) and neutralized with concentrated HCl to adjust the pH to 1-2 while keeping the temperature below 5° C. The precipitate is collected by filtration, rinsed with H2O (80 mL) and dried in vacuo to afford the product, 4-chloro-2-methylthiophene-3-carboxylic acid (F-7).

Workup

  1. customar RT
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue is poured into ice water (30 mL) and neutralized with concentrated HCl
  5. customthe temperature below 5° C
  6. filtrationThe precipitate is collected by filtration
  7. washrinsed with H2O (80 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-dc5779469a3945fd987df724e73227df
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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