Toluene → Octadecyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

HRID 640028

Reaktionsgleichung

Reaktionsgleichung von HRID 640028
[CH2:1]([OH: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][CH2:16][CH2:17][CH3:18].[O:20]1[CH:26]2[CH:21]1[CH2:22][CH:23]([C:27](OC)=[O:28])[CH2:24][CH2:25]2.N12CCN(CC1)CC2.C1(C)C=CC=CC=1>CO>[O:20]1[CH:26]2[CH:21]1[CH2:22][CH:23]([C:27]([O:19][CH2:1][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][CH2:16][CH2:17][CH3:18])=[O:28])[CH2:24][CH2:25]2

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8221Stearyl AlcoholHCID 9237DabcoHCID 127701647-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester

Produkt 1

HCID 22712608Octadecyl 7-oxabicyclo[4.1.0]heptane-3-carboxylateAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a 3-neck 100 mL flask equipped with an argon inlet, stir bar and distillation apparatus was added 1-octadecanol (5.03 g, 19 mmol, obtained from Sigma-Aldrich), methyl 3,4-epoxycyclohexanecarboxylate (ERL-4140, 8.69 g, 56 mmol, obtained from Dow Chemical Company), 1,4-diazabicyclo[2.2.2]octane (DABCO™, 1.02 g, 9.1 mmol, obtained from Sigma-Aldrich) and toluene (15 mL). The reaction mixture was refluxed until methanol ceased collecting in the receiving flask and the completion of the reaction was confirmed by 1H NMR spectroscopy. The still pot from the distillation was diluted with toluene (15 mL) and washed with brine (3×15 mL). The organic layer was separated, dried over MgSO4 and filtered. The solvent was removed in vacuo. The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum to give 6.78 g (87%) of a white solid (mp=32-34° C.) of octadecyl 3,4-epoxycyclohexanecarboxylate. 1H NMR (CDCl3, δ): 4.06 (td, J=6.7, 1.9 Hz, 2H), 3.25-3.14 (m, 2H), 2.55-2.45 (m, 1H), 2.31-1.26 (m, 38H), 0.88 (t, J=6.7 Hz, 3H).

Aufarbeitung

  1. customTo a 3-neck 100 mL flask equipped with an argon inlet
  2. distillationdistillation apparatus
  3. customceased collecting in the receiving flask
  4. distillationThe still pot from the distillation
  5. additionwas diluted with toluene (15 mL)
  6. washwashed with brine (3×15 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed in vacuo
  11. customThe excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dc937fcd3d9d44049590f1e51fa2e5d5
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691920B2

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