Water → 5,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

HRID 2118764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118764
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][C:16](O)=[O:17])[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7]([OH:19])([CH2:15][CH2:16][OH:17])[CH2:8]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 201931955,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 201932595,8-Dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

15.5 g of 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneacetic acid in 150 ml of tetrahydrofuran were added dropwise within 15 minutes to 3.32 g of lithium aluminum hydride in 150 ml of tetrahydrofuran. The reaction mixture was heated to reflux for 1 hour and then cooled. After the dropwise addition of 15 ml of ethyl acetate and 20 ml of water the suspension was filtered and the filtrate was concentrated. The product was purified by column chromatography (silica gel, chloroform/methanol 30:1). There was obtained 5,8-dimethoxy-1,2,3,4-tetrahydro-2-hydroxy-2-naphthaleneethanol, m.p. 121°-122°.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customThe product was purified by column chromatography (silica gel, chloroform/methanol 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-e5c5f0ec6ca846a98812021bed316aab
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04680310

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