Sulfuric Acid → HCID 15712395, compound

HRID 488692Notes

Reaction equation

HRID 488692 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([S:22]C(=O)N(C)C)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].S(=O)(=O)(O)O>C(O)C>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([SH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 15712394Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrate

Product 1

HCID 15712395HCID 15712395, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrate (10.6 g) and potassium hydroxide (4.5 g) in ethanol (100 ml) were heated with stirring under refluxing for 1.5 hours. Ice water and conc. sulfuric acid were added thereto (pH 1), and then the mixture was subjected to extraction. The organic layer was washed with water and aqueous solution of sodium chloride, followed by being dried over sodium sulfate and then concentrated under a reduced pressure. To the resultant residue was added a mixture of ethanol (30 ml) and conc. sulfuric acid (0.5 ml), and the mixture was heated with stirring and refluxing for 1.5 hours. Ice water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and thereafter was dried over sodium sulfate, followed by being concentrated under a reduced pressure. Ethyl 4-(6-acetyl-3-mercapto-2-propylphenoxy)butyrate (7.8 g, 89.7%) was obtained as brown oil.

Workup

  1. temperatureunder refluxing for 1.5 hours
  2. extraction(pH 1), and then the mixture was subjected to extraction
  3. washThe organic layer was washed with water and aqueous solution of sodium chloride
  4. dry with materialby being dried over sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. additionTo the resultant residue was added
  7. additiona mixture of ethanol (30 ml) and conc. sulfuric acid (0.5 ml)
  8. temperaturethe mixture was heated
  9. stirringwith stirring
  10. temperaturerefluxing for 1.5 hours
  11. additionIce water was added
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe organic layer was washed with water
  14. dry with materialwas dried over sodium sulfate
  15. concentrationby being concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a1f60c7ea09d445a9dbfb626497a2f06
Source dataset
uspto-grants-2005_12
Patent number
USRE038921E1

Reaction notes

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