Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → [2-(4-Methoxyphenyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid

HRID 280536Notes

Reaction equation

HRID 280536 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C([O:22][C:23]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:24])C>C1(C)C=CC=CC=1>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([CH2:25][C:23]([OH:24])=[O:22])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 3688143HCID 3688143, compound

Product 1

HCID 14815080[2-(4-Methoxyphenyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-hydroxy-2-(4-methoxyphenyl)isoindolin-1-one (12.0 g) and ethoxycarbonylmethylenetriphenylphosphorane (16.0 g) in toluene (200 ml) was refluxed for 3 hours. After cooling, the toluene was distilled off and the residue was dissolved in 100 ml of methanol. A solution of 10 g of potassium carbonate in 70 ml of water was added to the above methanol solution and the mixture was refluxed gently for an hour. After cooling, 200 ml of water and 300 ml of ether were added and the mixture was shaken well. The aqueous layer was separated and acidified with 5N hydrochloric acid to give 12 g of 3oxo-2-(4-methoxyphenyl)isoindoline-1-acetic acid, which was described in (iv) of Example 2.

Workup

  1. temperatureAfter cooling
  2. distillationthe toluene was distilled off
  3. dissolutionthe residue was dissolved in 100 ml of methanol
  4. additionA solution of 10 g of potassium carbonate in 70 ml of water was added to the above methanol solution
  5. temperaturethe mixture was refluxed gently for an hour
  6. temperatureAfter cooling
  7. addition200 ml of water and 300 ml of ether were added
  8. customThe aqueous layer was separated

Sources & evidence

ORD record
ord-99d02381671a4c3f9ee58b2a562bfb09
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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