p-Toluenesulfonic acid → HCID 15231340, compound

HRID 1885609Notes

Reaction equation

HRID 1885609 reaction equation
[CH3:1][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[CH3:8].[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][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[CH3:8]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 198793502-{[(3,4-Dimethylphenyl)sulfanyl]methyl}pentanedioic acid

Product 1

HCID 15231340HCID 15231340, compoundYield 1,423.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(3,4-dimethylphenylthiomethyl)glutaric acid (1.16 g), methanol (20 ml), and p-toluenesulfonic acid (0.04 g) was stirred at 40° C. for 1.5 hours. The reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography on silica by eluting with chloroform/ethanol (10:1) to give 0.98 g of 3-(3,4-dimethylphenylthio)-2-(2-methoxycarbonylethyl)propionic acid as an oil.

Workup

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

Sources & evidence

ORD record
ord-89d24beef4a24e86b630e004d2cc6883
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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