Citric Acid → [4-Hydroxy-3'-(hydroxymethyl)-6-methylbiphenyl-2-yl]methyl acetate

HRID 1908894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908894
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12]C(=O)C)[CH:9]=[C:8]([CH3:16])[C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=1)(=[O:3])[CH3:2].O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:16])[C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][OH:24])[CH:18]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59342569(4-Acetoxy-3'-formyl-6-methylbiphenyl-2-yl)methyl acetate

Produkt 1

HCID 59342611[4-Hydroxy-3'-(hydroxymethyl)-6-methylbiphenyl-2-yl]methyl acetateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (4-acetoxy-3′-formyl-6-methylbiphenyl-2-yl)methyl acetate (1.63 g, 4.99 mmol) in a mixed solvent of tetrahydrofuran (10 mL) and methanol (5 mL) was added sodium borohydride (90%, 0.210 g, 5.00 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 3 hr under nitrogen atmosphere. Aqueous citric acid solution was added to the reaction mixture, 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 residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20) to give the title compound (1.02 g, yield 71%) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20)

Quellen und Nachweise

ORD-Eintrag
ord-20aeef64b31e40f7961eaa5b46f9ece7
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598226B2

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