p-Toluenesulfonic acid → HCID 15234813, compound

HRID 1645782Notes

Reaction equation

HRID 1645782 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:12][CH:13]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:14]([OH:16])=[O:15].[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:22][O:20][C:19]([CH2:18][CH2:17][CH:13]([CH2:12][S:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:14]([OH:16])=[O:15])=[O:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15234818HCID 15234818, compound

Product 1

HCID 15234813HCID 15234813, compoundYield 1,646.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(2-naphthylthiomethyl)glutaric acid (28.8 g), methanol (300 ml), and p-toluenesulfonic acid (0.9 g) was stirred at 40° C. for 2.5 hours. The reaction mixture was concentrated in vacuo, and water was added to the resulting residue. The mixture was extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized from isopropyl ether to give 27.4 g of 2-(2-methoxycarbonylethyl)-3-(2-naphthylthio)propionic acid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and water
  2. additionwas added to the resulting residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-e439eed0604d4e4eaee820ee63d1c722
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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