Acetic Acid → 4-Acetoxybenzyl alcohol

HRID 446198

Reaktionsgleichung

Reaktionsgleichung von HRID 446198
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na].C(O)(=O)C.O>CO>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 70144Benzaldehyde, 4-(acetyloxy)-HCID 5360545Sodium

Produkt 1

HCID 959064-Acetoxybenzyl alcoholAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To the solution of 4-formylphenol acetate (6.0 g, 36.4 mmol) in 60 ml of methanol was added sodium boronhydride (1.50 g, 39.6 mmol) at 0° C. The resultant mixture was stirred for 1 hour, neutralized with acetic acid and then poured into water. The mixture was extracted three times with ether and the combined organic layer was dried over magnesium sulfate. After removal of solvent, the compound was purified by flash chromatography using heptane/ethyl acetate (80/20-70/30) as eluent in a yield of 41%.

Aufarbeitung

  1. extractionThe mixture was extracted three times with ether
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. customAfter removal of solvent
  4. customthe compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-71d6abc2e19f49eb966ff1acf7270756
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476450B2

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