Hydrochloric Acid → 5-Tert-butyl-3-nitrothiophene-2-carboxylic acid

HRID 18921Notes

Reaction equation

HRID 18921 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([O:12]C)=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.Cl>O>[C:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 58679165Methyl 5-tert-butyl-3-nitrothiophene-2-carboxylate

Product 1

HCID 586792065-Tert-butyl-3-nitrothiophene-2-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

LiOH monohydrate (0.122 g, 2.90 mmol) was dissolved in 1 mL water and added to methyl 5-tert-butyl-3-nitrothiophene-2-carboxylate (0.235 g, 0.966 mmol) in 3 ml of a 3:1 mixture of THF:MeOH. The resulting mixture was heated at 75° C. for 5 hours. The reaction was cooled down to room temperature, acidified with 1N HCl, extracted with ethyl acetate, and the crude product was recrystallized from dichloromethane:hexane to afford 0.214 g of 5-tert-butyl-3-nitrothiophene-2-carboxylic acid as a yellow solid.

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. customthe crude product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-c84dfea3f23a4a7a83219cb416ea6adc
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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