1-Tetradecanol → 1,2-Epoxy-2-methyl-3-tetradecyloxypropane

HRID 1102

Reaktionsgleichung

Reaktionsgleichung von HRID 1102
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].C(Cl)C(=C)C.ClC1C=C[CH:27]=[C:26]([C:30]([O:32]O)=O)[CH:25]=1>ClCCl.O.CN(C)C=O>[O:32]1[C:26]([CH3:27])([CH2:25][O:15][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][CH3:14])[CH2:30]1

Komponenten

8

Edukt 4

HCID 82091-TetradecanolHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acid

Produkt 1

HCID 196946081,2-Epoxy-2-methyl-3-tetradecyloxypropaneAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 200-ml flask equipped with a stirrer was charged with 10 g (46.6 mmol) of tetradecanol, 50 ml of dimethylformamide, 2.86 g (71.5 mmol) of 60% NaH and 5.96 g (65.8 mmol) of methallyl chloride. The contents were stirred at 60° C. for 15 hours. After completion of the reaction, the reaction mixture was added with water and subjected to extraction with hexane, and the solvent was distilled off under reduced pressure. The resultant residue was charged into a 300-ml flask equipped with a stirrer, and 12.24 g (70.9 mmol) of m-chloroperbenzoic acid and 200 ml of dichloromethane were added thereto. The resultant mixture was stirred at room temperature for 19 hours. Solids formed were separated by filtration, and the resultant solution was concentrated under reduced pressure and then purified by column chromatography on silica gel, thereby obtaining 10.54 g (yield: 79.4%) of 1,2-epoxy-2-methyl-3-tetradecyloxypropane as an intermediate.

Aufarbeitung

  1. customA 200-ml flask equipped with a stirrer
  2. customAfter completion of the reaction
  3. extractionsubjected to extraction with hexane
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe resultant residue was charged into a 300-ml flask
  6. customequipped with a stirrer
  7. customSolids formed
  8. customwere separated by filtration
  9. concentrationthe resultant solution was concentrated under reduced pressure
  10. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cb6871243aa046c0acd17a0fc444cdcb
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723497

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