Hydrochloric Acid → 4-Mercapto-2-propylphenoxy-acetic acid ethyl ester

HRID 898484Notes

Reaction equation

HRID 898484 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=O)=O)=[CH:9][C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[Sn].Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 207681244-Chlorosulfonyl-2-propylphenoxy-acetic acid ethyl ester

Product 1

HCID 207681114-Mercapto-2-propylphenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4-chlorosulfonyl-2-propyl-phenoxy)-acetic acid ethyl ester (1.12 g, 3.5 mmol), tin powder (2.1 g) and HCl (4.0 M in dioxane, 4.4 mL) in ethanol (4.4 mL) was refluxed for 4 h, the mixture was poured into ice, extracted with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, concentrated to give the title compound, which was used for next step without purification.

Workup

  1. temperaturewas refluxed for 4 h
  2. additionthe mixture was poured into ice
  3. extractionextracted with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0185e1f03d6849c783ddcd7ea25475a0
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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