Hydrochloric Acid → (4-Mercapto-phenoxy)-acetic Acid Ethyl Ester

HRID 854530Notes

Reaction equation

HRID 854530 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=O)=O)=[CH:9][CH:8]=1)[CH3:2].[Sn].Cl.C(Cl)Cl>C(O)C.O1CCOCC1>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([SH:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 5352426Tin atomHCID 14721760Ethyl 4-chlorosulfonylphenoxyacetate

Product 1

HCID 57431967(4-Mercapto-phenoxy)-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (4-chlorosulfonyl-phenoxy)-acetic acid ethyl ester (0.98 g, 3.5 mmol) and tin powder (2.1 g) in ethanol (4.4 mL) is added HCl in dioxane (1.0 M, 4.4 mL) under nitrogen. The mixture is heated to reflux for 2 hrs, it is poured into ice and methylene chloride and filtered. The layers are separated and extracted with methylene chloride, dried and concentrated. The crude product is used for next step without purification.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 2 hrs
  3. filtrationfiltered
  4. customThe layers are separated
  5. extractionextracted with methylene chloride
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product is used for next step without purification

Sources & evidence

ORD record
ord-52d965e468fb4322a155f24b5deca6fe
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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