p-Toluenesulfonic acid → HCID 15228403, compound

HRID 1885602Notes

Reaction equation

HRID 1885602 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 198793472-{[(3,4-Dichlorophenyl)sulfanyl]methyl}pentanedioic acid

Product 1

HCID 15228403HCID 15228403, compoundYield 1,656.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(3,4-dichlorophenylthiomethyl)glutaric acid (3.00 g), methanol (30 ml), and p-toluenesulfonic acid (0.09 g) was stirred at 40° C. for 2.5 hours. The reaction mixture was concentrated in vacuo, and the resulting residue was purified by flash column chromatography on silica by eluting with chloroform/ethanol (10:1) to give 2.92 g of 3-(3,4-dichlorophenylthio)-2-(2-methoxycarbonylethyl)propionic acid as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by flash column chromatography on silica
  3. washby eluting with chloroform/ethanol (10:1)

Sources & evidence

ORD record
ord-d33357b1d12e4b5994000da56ddcd000
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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