Methanol → HCID 66713069, compound

HRID 409219Notes

Reaction equation

HRID 409219 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH2:15][C:16]([OH:18])=[O:17])[C:8]2=[O:19].S(=O)(=O)(O)O.[CH3:30]O>O>[CH3:30][O:17][C:16](=[O:18])[CH2:15][N:9]1[C:8](=[O:19])[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([O:4][C:3]3[C:2]([CH3:1])=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:24])[CH:6]=2)[C:10]1=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67110507HCID 67110507, compound

Product 1

HCID 66713069HCID 66713069, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of [5-(2,6-Dimethyl-phenoxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid in MeOH (1 mL/mmol) was added concentrated sulfuric acid (35 μl/mmol) and the mixture was refluxed with stirring for 16 h before it was diluted with water (6.5 mL/mmol) and extracted twice with EtOAc. The combined organic phases were washed with saturated NaHCO3 solution, dried over MgSO4, and concentrated in vacuo to give the title compound as a tan solid (yield: 96%); MS-(+)-ion: M+1=340.5.

Workup

  1. temperaturethe mixture was refluxed
  2. extractionextracted twice with EtOAc
  3. washThe combined organic phases were washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b696344a7d6a499f8b79535e852fbd9e
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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