Benzaldehyde → HCID 15641097, Verbindung

HRID 533182

Reaktionsgleichung

Reaktionsgleichung von HRID 533182
[CH2:1]([OH:7])[CH:2]([OH:6])[CH2:3][CH2:4][OH:5].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:7][CH2:1][CH:2]1[CH2:3][CH2:4][O:5][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6]1

Komponenten

5

Edukt 2

HCID 240BenzaldehydeHCID 183021,2,4-Butanetriol

Produkt 1

HCID 15641097HCID 15641097, VerbindungAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1,2,4-butanetriol (3.0 g, 28.3 mmol) and benzaldehyde (11.48 ml, 113 mmol) in dry toluene (50 mL) with p-toluenesulfonic acid monohydrate (0.269 g, 1.413 mmol) was heated under reflux in a Dean-Stark apparatus. After ˜1 h, the solution was washed with sat. aq NaHCO3, dried and concentrated under high vac to remove most of the benzaldehyde. Chromatography gave syrupy title compound (2.88 g, 14.83 mmol, 52.5% yield). The NMR's were the same as reported (Tetrahedron Asymm. 1996, 7, 3209-3246).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux in a Dean-Stark apparatus
  3. washthe solution was washed with sat. aq NaHCO3
  4. customdried
  5. concentrationconcentrated under high vac
  6. customto remove most of the benzaldehyde

Quellen und Nachweise

ORD-Eintrag
ord-02b36c42d66346ff9c6707989ca20401
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853224B2

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