Benzyl formate → HCID 54271345, Verbindung

HRID 476349

Reaktionsgleichung

Reaktionsgleichung von HRID 476349
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(O[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O>CCCCCCCC>[CH2:24]([O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 7708Benzyl formate2×HCID 10459Hexadecanedioic acid

Produkt 1

HCID 54271345HCID 54271345, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 356OctaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Hexadecanedioic acid (20.0 g, 69.8 mmol) and Dowex® were suspended in n-octane and heated to reflux. Benzyl formate (22.0 g, 162 mmol) was added. After 6 hours additional benzyl formate (22.0 g, 162 mmol) was added. The heating was continued for 50 hours. The reaction mixture was filtered at 80° C. The filtrate was cooled to 20° C., and the precipitate was collected by filtration. The crude product (20.2 g) was suspended in dichloromethane (220 ml) at 20° C. for 4 hours. The suspension was filtered, and the filtrate was evacuated to dryness at 20-30° C. The resulting solid (13.9 g) was recrystallised from 2-propanol (140 ml). The product was isolated by filtration, and dried to constant weight under reduced pressure at 30-40° C. Yield: 10.2 g (39%) of white material.

Aufarbeitung

  1. temperatureheated to reflux
  2. filtrationThe reaction mixture was filtered at 80° C
  3. filtrationthe precipitate was collected by filtration
  4. waitThe crude product (20.2 g) was suspended in dichloromethane (220 ml) at 20° C. for 4 hours
  5. filtrationThe suspension was filtered
  6. customthe filtrate was evacuated to dryness at 20-30° C
  7. customThe resulting solid (13.9 g) was recrystallised from 2-propanol (140 ml)
  8. customThe product was isolated by filtration
  9. customdried to constant weight under reduced pressure at 30-40° C

Quellen und Nachweise

ORD-Eintrag
ord-5fac0035e8e44bb585875c74861c995b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637647B2

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