Ethanol → 4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

HRID 23600

Reaktionsgleichung

Reaktionsgleichung von HRID 23600
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.O1CCCC1.C(O)C>ClCCl.[Pd]>[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

6

Edukt 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 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 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A flask equipped with magnetic stirrer was charged with 5-(benzyloxy)-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol (14.5 g, 42.8 mmol) and tetrahydrofuran (50 ml) and ethanol (100 ml) and palladium (4.54 g, 10% on activated carbon) were added sequentially. The reaction vessel was then evacuated, placed under a hydrogen atmosphere and stirred vigorously for 24 hr. The reaction mixture was filtered through a celite plug, washing with ethyl acetate. The filtrate was concentrated in vacuo to give an off white solid. The crude solid was slurried in dichloromethane (200 ml), affording the title compound (10.2 g, 95%) as a white solid. m/z(ES+) 251(M+H+).

Aufarbeitung

  1. customA flask equipped with magnetic stirrer
  2. additionwere added sequentially
  3. customThe reaction vessel was then evacuated
  4. filtrationThe reaction mixture was filtered through a celite plug
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an off white solid

Quellen und Nachweise

ORD-Eintrag
ord-20dfcce9f0c546d8b9b04dcc962410fc
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852747B2

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