Reaktion #1366316

ord-5e69fe56e7e042fd9f6eb6361228f83f

Reaktionsgleichung

O=C1CCCCCCCCCCCCCCCO1
16-Hexadecanolide
I
HI
O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulphate
→
O=C(O)CCCCCCCCCCCCCCCI
16-Iodohexadecanoic Acid

Edukte

O=C1CCCCCCCCCCCCCCCO1
16-Hexadecanolide
I
HI
O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulphate

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling it
  2. 2
    Extraktionextracted
  3. 3
    TrocknenThe combined organic extracts were dried (MgSO4)
  4. 4
    Sonstigeevaporated
  5. 5
    Sonstigeto give a white solid
  6. 6
    SonstigeThe crude product was recrystallised from diethyl ether

Vorschrift

16-Hexadecanolide (5.0 g, 0.02 mol) was added to a mixture of HI (30 g) and acetic acid (20 g). The mixture was heated to 100° C. overnight. After cooling it was poured into a cold sodium thiosulphate solution (150 mL, 10%) and extracted using CH2Cl2. The combined organic extracts were dried (MgSO4) and evaporated to give a white solid. The crude product was recrystallised from diethyl ether. Yield: 4.8 g (64%)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06447656B1uspto-grants-2002_09