Sulfuric Acid → (1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester

HRID 250365

Reaktionsgleichung

Reaktionsgleichung von HRID 250365
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)CCC>[CH2:4]([O:14][C:13](=[O:15])[CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:5][CH2:6][CH3:7]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 20825N-PhthaloylglycineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 357739(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl esterAusbeute 194,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 160 ml of butanol, 20.0 g of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid (94.6 mmol) and 2.0 ml of concentrated sulfuric acid was refluxed with stirring for 24 h. Then 5 g of sodium bicarbonate were added in portions, stirring continued at r.t. for 5 min and the solvent evaporated in vacuo. The residue was partitioned between 100 ml of water and 100 ml of ethyl acetate. The organic phase was washed with 100 ml of brine, dried over sodium sulfate and was evaporated in vacuo to give a yellowish oil that later solidified. 24.02 g of the title compound were obtained; MS-(+)-ion: M+1=261.9.

Aufarbeitung

  1. temperaturewas refluxed
  2. stirringstirring
  3. waitcontinued at r.t. for 5 min
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of water and 100 ml of ethyl acetate
  6. washThe organic phase was washed with 100 ml of brine
  7. dry with materialdried over sodium sulfate
  8. customwas evaporated in vacuo
  9. customto give a yellowish oil that

Quellen und Nachweise

ORD-Eintrag
ord-617796caf49848efaa5247e234cb088c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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