Methanol → (6'-Hydroxymethyl-4,6,2',4'-tetramethoxy-biphenyl-2-yl)-methanol

HRID 417694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417694
CO.C[O:4][C:5]([C:7]1[C:8]([C:17]2[C:18]([C:27](OC)=[O:28])=[CH:19][C:20]([O:25][CH3:26])=[CH:21][C:22]=2[O:23][CH3:24])=[C:9]([O:15][CH3:16])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:4][CH2:5][C:7]1[C:8]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=2[CH2:27][OH:28])=[C:9]([O:15][CH3:16])[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 120747334,6,4',6'-Tetramethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10958571(6'-Hydroxymethyl-4,6,2',4'-tetramethoxy-biphenyl-2-yl)-methanolAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(6′-Hydroxymethyl-4,6,2′,4% tetramethoxy-biphenyl-2-yl)-methanol: 4,6,4′,6′-tetramethoxy-biphenyl-2,2′-dicarboxylic acid dimethyl ester (2.5 g) was dissolved in THF (96 mL), and 1M LiAlH4 in THF (9.6 mL) was added. After stirring at room temperature for overnight, the mixture was quenched with water and 2N HCl (24 mL) was added. The mixture was evaporated under vacuum and partitioned with DCM (300 mL) and water (200 mL). The organic layer was dried over Na2SO4 and crystallized with DCM to provide (6′-hydroxymethyl-4,6,2′,4′-tetramethoxy-biphenyl-2-yl)-methanol (1.7 g, 77%) as a pale blue white triclinic crystals.

Aufarbeitung

  1. customthe mixture was quenched with water and 2N HCl (24 mL)
  2. additionwas added
  3. customThe mixture was evaporated under vacuum
  4. custompartitioned with DCM (300 mL) and water (200 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customcrystallized with DCM

Quellen und Nachweise

ORD-Eintrag
ord-0ba125f783b64500a0798e289e67179c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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