Resorcinol → 3-[(Tert-butyldimethylsilyl)oxy]phenol

HRID 1986373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986373
[C:1]1([OH:8])[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.Cl[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[C:13]([Si:10]([CH3:12])([CH3:11])[O:7][C:3]1[CH:2]=[C:1]([OH:8])[CH:6]=[CH:5][CH:4]=1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 5054ResorcinolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 114474403-[(Tert-butyldimethylsilyl)oxy]phenolAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,3-Benzenediol (5 g, 45 mmol) in dichloromethane (150 mL) was treated with chloro(t-butyl)dimethylsilane (7.5 g, 50 mmol) and triethylamine (5 g, 50 mmol). The resulting mixture was stirred at rt for 16 h then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was washed with 6N NaOH, then concentrated in vacuo. The residue was purified by column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound (4.3 g, 42%). MS (ES+) m/e 225 [M+H]+.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with 6N NaOH
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-bfd0744ece5f4548aaf1fc39583f6b9c
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547779B2

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