Dicyclohexylcarbodiimide → 1,4,8-Trioxaspiro[4.5]decane-7,9-dione

HRID 231247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231247
[CH2:1]1[CH2:13][O:12][C:3]([CH2:8][C:9]([OH:11])=[O:10])([CH2:4][C:5](O)=[O:6])[O:2]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:1]1[CH2:13][O:12][C:3]2([CH2:8][C:9](=[O:11])[O:10][C:5](=[O:6])[CH2:4]2)[O:2]1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 133834462,2'-(1,3-Dioxolane-2,2-diyl)diacetic acid

Produkt 1

HCID 133834501,4,8-Trioxaspiro[4.5]decane-7,9-dioneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3,3-(ethylenedioxy)glutaric acid (12.26 g, 64.50 mmole) in 300 ml of tetrahydrofuran maintained at 0° C. under nitrogen was added dropwise a solution of dicyclohexylcarbodiimide (13.60 g, 65.91 mmole) in 100 ml of tetrahydrofuran. The resulting suspension was stirred at room temperature overnight under nitrogen and the solvent was evaporated under vacuum. The residue was suspended in benzene, shaken thoroughly and filtered through silica gel packed in a column (10 cm long, SiO2, 60-200 mesh, benzene). The filtrate was evaporated under vacuum to provide the anhydride (8.268 g, 75% yield) as a white crystalline solid melting at about 111° C. to about 112° C.

Aufarbeitung

  1. customthe solvent was evaporated under vacuum
  2. stirringshaken thoroughly
  3. filtrationfiltered through silica gel
  4. customThe filtrate was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8b97b802c4064ba09ec68d8565a93d00
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845229

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