Methanol → 3'-(Hydroxymethyl)-2,6-dimethylbiphenyl-4-ol

HRID 416150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416150
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.CO.[BH4-].[Na+]>O1CCCC1>[OH:16][CH2:15][C:11]1[CH:10]=[C:9]([C:5]2[C:4]([CH3:17])=[CH:3][C:2]([OH:1])=[CH:7][C:6]=2[CH3:8])[CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Produkt 1

HCID 593425523'-(Hydroxymethyl)-2,6-dimethylbiphenyl-4-olAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (6.95 g, 30.7 mmol) in a mixed solvent of methanol (30 mL) and tetrahydrofuran (60 mL) was ice-cooled, sodium borohydride (90%, 1.29 g, 30.7 mmol) was added, and the mixture was stirred for 20 hr under nitrogen atmosphere, during which the mixture was allowed to gradually warm to room temperature. The reaction mixture was concentrated under reduced pressure, the residue was treated with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (6.56 g, yield 93%) as colorless crystals.

Aufarbeitung

  1. temperaturecooled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was treated with diluted hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crystals were recrystallized from heptane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8224df8df5ce43fbb89754703fd3a940
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088821B2

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