Phthalic Anhydride → 2-(1-hydroxy-2-methylpropan-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 872519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872519
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]1(=O)[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>>[OH:4][CH2:3][C:2]([N:1]1[C:10](=[O:11])[C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]1=[O:12])([CH3:6])[CH3:5]

Komponenten

3

Edukt 2

HCID 6811Phthalic AnhydrideHCID 118072-Amino-2-methyl-1-propanol

Produkt 1

HCID 8277892-(1-hydroxy-2-methylpropan-2-yl)-2,3-dihydro-1H-isoindole-1,3-dioneAusbeute 33 %

Versuchsvorschrift

2-Amino-2-methyl-1-propanol (4.46 g, 50 mmol) and phthalic anhydride (7.41 g, 50 mmol) were heated at 170° C. for 30 minutes. Icewater was added to the cooled reaction mixture and then the mixture was extracted three times with DCM. Organic phase was dried over Na2SO4, filtered and evaporated to dryness. Crude product was purified by CombiFlash (column: silica, eluent: 0-10% MeOH in DCM) to obtain 3.611 g (33%) of the title compound. LC-MS: M+1=220.

Aufarbeitung

  1. additionIcewater was added to the cooled reaction mixture
  2. extractionthe mixture was extracted three times with DCM
  3. dry with materialOrganic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customCrude product was purified by CombiFlash (column: silica, eluent: 0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-efb87f9e720c4e02b222321f0d65bf58
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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