3,4-Dichlorobenzenethiol → 3-(3,4-Dichlorophenylthio)-2-methoxycarbonylmethylpropionic acid

HRID 1885605Notes

Reaction equation

HRID 1885605 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:10][O:11][C:12]([CH2:14][C:15](=[CH2:19])[C:16]([O-:18])=[O:17])=[O:13].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:19][CH:15]([CH2:14][C:12]([O:11][CH3:10])=[O:13])[C:16]([OH:18])=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 799643,4-DichlorobenzenethiolHCID 23678954Sodium 3-methoxycarbonyl-2-methylenepropionate

Product 1

HCID 198793483-(3,4-Dichlorophenylthio)-2-methoxycarbonylmethylpropionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 3,4-dichlorobenzenethiol (1.15 ml), sodium 3-methoxycarbonyl-2-methylenepropionate (1.50 g), methanol (40 ml), and triton B (40% methanol solution, 5 drops) was refluxed for 20 hours. The reaction mixture was concentrated in vacuo. To the resulting residue was added a diluted hydrochloric acid, and a separated oil was extracted with diethyl ether. The organic layer was washed with water, dried over MgSO4, and evaporated at reduced pressure. The residue was purified by flash column chromatography on silica by eluting with chloroform/ethanol (10:1) to give 2.34 g of 3-(3,4-dichlorophenylthio)-2-methoxycarbonylmethylpropionic acid as an oil.

Workup

  1. temperaturewas refluxed for 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionTo the resulting residue was added a diluted hydrochloric acid
  4. extractiona separated oil was extracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated at reduced pressure
  8. customThe residue was purified by flash column chromatography on silica
  9. washby eluting with chloroform/ethanol (10:1)

Sources & evidence

ORD record
ord-5e25916da5074992bcf8718e0e15698d
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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