Diethyl Ether → 2-Hydroxymethyl-5,6,7-trimethoxynaphthalene

HRID 720302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720302
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([C:23](O)=[O:24])=[CH:14]2.CCOCC.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:24][CH2:23][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[C:18]([O:19][CH3:20])[C:9]=2[O:8][CH3:7])[CH:14]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 62649Sodium sulfate decahydrateHCID 30179615,6,7-Trimethoxy-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 218915782-Hydroxymethyl-5,6,7-trimethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (579 mg) was added to dry THF (40 mL) under an argon atmosphere and ice cooling, a solution of 5,6,7-trimethoxynaphthalene-2-carboxylic acid (4.0 g) in dry THF (40 mL) was then added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. Ether (150 mL) was added to the reaction mixture, sodium sulfate decahydrate was added thereto, and the resultant mixture was stirred for 15 minutes. The reaction mixture was filtered, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Aufarbeitung

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-9496f69053604f698aa27c6c6908ce65
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135473B2

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