Sodium Hydroxide → 3-Chloro-5-methylthiophene-2-carboxylic acid

HRID 370080Notes

Reaction equation

HRID 370080 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1[Cl:10])=[O:4].[OH-].[Na+]>C(O)C>[C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1[Cl:10])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18376623Methyl 3-chloro-5-methylthiophene-2-carboxylate

Product 1

HCID 166400013-Chloro-5-methylthiophene-2-carboxylic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methoxycarbonyl-3-chloro-5-methylthiophene (1.3 g, 6.8 mmol) in ethanol (16 mL) was added aqueous sodium hydroxide (1 N, 16 mL, 16 mmol) and the mixture stirred at ambient temperature. After 3 hours the mixture was concentrated of all volatiles in vacuo. The residual solid was dissolved in water (60 mL), acidified with 1 N HCl and the solid collected by filtration to afford 1.2 g (95% yield) of 2-carboxy-3-chloro-5-methylthiophene as a white solid; NMR (CDCl3) 6.8 (s, 1), 2.5 (s, 3) ppm.

Workup

  1. concentrationAfter 3 hours the mixture was concentrated of all volatiles in vacuo
  2. dissolutionThe residual solid was dissolved in water (60 mL)
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-65367322375f44d6ae1d5eaadbee0047
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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