Hydrochloric Acid → (4-Cyclopropylsulfanylphenyl)oxoacetic acid

HRID 546234Notes

Reaction equation

HRID 546234 reaction equation
C([O:3][C:4](=[O:17])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)=[O:6])C.[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH:14]1([S:13][C:10]2[CH:9]=[CH:8][C:7]([C:5](=[O:6])[C:4]([OH:17])=[O:3])=[CH:12][CH:11]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46856411Ethyl [4-(cyclopropylsulfanyl)phenyl](oxo)acetate

Product 1

HCID 21094072(4-Cyclopropylsulfanylphenyl)oxoacetic acidYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In a flask (4-cyclopropylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (9.19 g, 36.71 mmol) was dissolved in toluene (20 mL) and heated to 50° C. in an oil bath. To this heated solution was then added an aqueous sodium hydroxide solution (3 M solution, 15.17 mL, 45.52 mmol) dropwise keeping the temperature of the reaction below 60° C. The reaction was then stirred at 50° C. for 1.5 h. After this time the reaction was removed from the oil bath and concentrated hydrochloric acid (3.5 mL, 42.2 mmol) was added dropwise while the reaction was still at 50° C. It was then allowed to cool to 25° C. and stirred for 16 h. The solids were filtered off and washed with water (10 mL) and toluene (10 mL) to afford (4-cyclopropylsulfanyl-phenyl)-oxo-acetic acid (3.41 g, 42%) as a white solid and used without purification.

Workup

  1. customthe temperature of the reaction below 60° C
  2. additionwas added dropwise while the reaction
  3. customwas still at 50° C
  4. temperatureto cool to 25° C.
  5. stirringstirred for 16 h
  6. filtrationThe solids were filtered off
  7. washwashed with water (10 mL) and toluene (10 mL)

Sources & evidence

ORD record
ord-a99b0f79d158455d824f1c897e3b0435
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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