Cornforth reagent → (E)-Hexadec-2-enal

HRID 1086006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1086006
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([OH:38])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>ClCCl>[CH:22](=[O:38])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 5362706(E)-Hexadec-2-en-1-ol

Produkt 1

HCID 5280541(E)-Hexadec-2-enalAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt. 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2CH2CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes): trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+).

Aufarbeitung

  1. filtrationthe mixture was filtered (through Celite diatomaceous earth)
  2. customThe colorless solution obtained
  3. concentrationwas concentrated in vacuo to 21.8 g (86%) of a white solid
  4. distillationDistillation (90-100° C./0.40-0.45 torr)

Quellen und Nachweise

ORD-Eintrag
ord-84278eda96424bf191448e417c5ca717
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05012000

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