m-Chloroperbenzoic acid → 1,2-Epoxy-1-(4-nonylphenyl)-hexane

HRID 1382700

Reaktionsgleichung

Reaktionsgleichung von HRID 1382700
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:23][CH:22]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>ClCCl>[O:9]1[CH:28]([CH2:29][CH2:30][CH2:31][CH3:32])[CH:27]1[C:24]1[CH:23]=[CH:22][C:21]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 536769591-(4-Nonylphenyl)-hex-1-ene

Produkt 1

HCID 212731161,2-Epoxy-1-(4-nonylphenyl)-hexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6.76 g of m-chloroperbenzoic acid (90% content) in 100 ml of dichloromethane are added to a solution of 6.32 g of 1-(4-nonylphenyl)-hex-1-ene (mixture of cis- and trans-isomers) from the preceding stage in 150 ml of dichloromethane while cooling to 0°-5°, and the whole is stirred for 20 hours at 20°. The rection mixture is washed in succession with 10% strength (w/v) sodium sulphite solution, 5% strength (w/v) sodium carbonate solution and 3 portions of water, dried over sodium sulphate and concentrated by evaporation. Chromatography of the residue on silica gel with hexane/ethyl acetate (19:1) yields in succession the trans-[1(RS),2(RS)-] and the cis-[1(RS),2(SR)-] -isomer in the form of colourless oils.

Aufarbeitung

  1. temperaturewhile cooling to 0°-5°
  2. washThe rection mixture is washed in succession with 10% strength (w/v) sodium sulphite solution, 5% strength (w/v) sodium carbonate solution and 3 portions of water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customChromatography of the residue on silica gel with hexane/ethyl acetate (19:1) yields in succession the trans-[1(RS),2(RS)-] and the cis-[1(RS),2(SR)-] -isomer in the form of colourless oils

Quellen und Nachweise

ORD-Eintrag
ord-b82e61b6a2494577bbb082eb6a9b7306
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808572

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