Hydrochloric Acid → 2-(5-t-Butylthiophen-2-yl)-cyclopropanecarboxylic acid

HRID 1252465Notes

Reaction equation

HRID 1252465 reaction equation
[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:12][CH:11]2[C:13]([O:15]CC)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl.[Cl-].[Na+]>CO.O>[C:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:12][CH:11]2[C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 20139953Ethyl 2-(5-t-butylthiophen-2-yl)-cyclopropanecarboxylate

Product 1

HCID 201399602-(5-t-Butylthiophen-2-yl)-cyclopropanecarboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(5-t-butylthiophen-2-yl)-cyclopropanecarboxylate (4.49 g, 0.018 mol) was dissolved in methanol (45 ml) and a solution of potassium hydroxide (1.99 g, 0.036 mol) in water (45 ml) added dropwise at room temperature. The solution was refluxed for 3 hours, cooled to room temperature and carefully neutralised with 2M HCl. Saturated sodium chloride was added, the aqueous solution extracted with ethyl acetate (4×50 ml) and dried over anhydrous sodium sulphate. Removal of the solvent gave 2-(5-t-butylthiophen-2-yl)-cyclopropanecarboxylic acid (3.79 g, 94%).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. extractionthe aqueous solution extracted with ethyl acetate (4×50 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-e413a4b1ed2845fabc670426f586192d
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Reaction notes

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