5-(Benzyloxy)2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol → 4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

HRID 585653

Reaktionsgleichung

Reaktionsgleichung von HRID 585653
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:16]2[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH:17]=2)=[C:13]([OH:15])[CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[O:20]1[C:19]2([CH2:24][CH2:25][CH:16]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][C:13]=3[OH:15])[CH2:17][CH2:18]2)[O:23][CH2:22][CH2:21]1

Komponenten

4

Edukt 1

HCID 117392405-(Benzyloxy)2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol

Produkt 1

HCID 99212574-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A round bottomed flask equipped with magnetic stirrer was charged with 5-(benzyloxy)-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol (6.90 g, 20.4 mmol), ethanol (300 ml) and palladium (2.00 g, 10% on activated carbon). The reaction vessel was then evacuated and placed under a hydrogen atmosphere. This process was repeated 15 times before stirring vigorously for 64 hr under a hydrogen atmosphere. The reaction mixture was filtered through a celite plug, washing with ethyl acetate. The filtrate was concentrated in vacuo, furnishing the title compound (5.10 g, 100%) as a solid. m/z (ES+) 251(M+H+).

Aufarbeitung

  1. customA round bottomed flask equipped with magnetic stirrer
  2. customThe reaction vessel was then evacuated
  3. filtrationThe reaction mixture was filtered through a celite plug
  4. washwashing with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-de68d828ba3e4511b6456d79b7022d42
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933319B2

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