p-Toluenesulfonic acid → 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid methyl ester

HRID 19553Notes

Reaction equation

HRID 19553 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([OH:21])[CH:9]=2)=[O:5])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][CH:11]=[C:10]([OH:21])[CH:9]=2)=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 118452796-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 687002636-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid methyl esterYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (500 mg, 1.70 mmol) prepared in Preparation Example 2 was dissolved in methanol (30 mL), p-toluenesulfonic acid (65 mg, 0.34 mmol) was added thereto, refluxed for 24 hrs, and the solvent was removed therefrom by evaporation. The resulting residue was purified by flash chromatography to obtain 470 mg of the titled compound (yield: 98.6%) as a red solid.

Workup

  1. temperaturerefluxed for 24 hrs
  2. customthe solvent was removed
  3. customby evaporation
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c58bfd6276374db59e66f17c0eef611d
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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