Water → HCID 14204115, Verbindung

HRID 1722373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1722373
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2.[OH:16][CH2:17][CH2:18]CCCC12CC(=O)CC1CCC2.O>C(O)(=O)C>[C:17]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2)(=[O:16])[CH3:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14204106HCID 14204106, VerbindungHCID 20028720HCID 20028720, Verbindung

Produkt 1

HCID 14204115HCID 14204115, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The starting material 2-(5-hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxypentyl)-2(1H)-pentalenone} (0.8 g, 3.8 mmoles) is diluted with glacial acetic acid (7 ml). The reaction is stirred and heated in a 75° C. oil bath for 24 hours, after which time water (20 ml) is added and the reaction partitioned between ether. The ether layer is separated and the aqueous phase extracted again with ether (2×50 ml). The extracts and the organic phase are combined and neutralized with saturated sodium bicarbonate. The organic phase is dried over anhydrous magnesium sulfate and the remained solvent removed under vacuum leaving a pale yellow oil. The product is kugelrohred under reduced pressure leaving a clear, colorless oil (0.5 g, 2.0 mmoles).

Aufarbeitung

  1. customthe reaction partitioned between ether
  2. customThe ether layer is separated
  3. extractionthe aqueous phase extracted again with ether (2×50 ml)
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. customthe remained solvent removed under vacuum
  6. customleaving a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-71ff3e66a9064a25ae0380a87a98dd39
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04855322

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