Dimethyl Sulfide → (Z,Z)-11,13-Hexadecadienal

HRID 2049844

Reaktionsgleichung

Reaktionsgleichung von HRID 2049844
ClN1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].CSC.C/C=[C:14](\[C:25]1C=C[C:28](O)=[CH:27][CH:26]=1)/[C:15](/[C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1)=C/C.C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH:3](=[O:8])[CH2:4][CH2:5][CH2:6][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:15]=[CH:14]\[CH:25]=[CH:26]/[CH2:27][CH3:28]

Komponenten

7

Edukt 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 667476Dienestrol

Produkt 1

HCID 6436739(Z,Z)-11,13-Hexadecadienal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a mixture of N-chlorosuccinimide (16.8 g, 0.126 mol) and 260 ml of toluene, cooled to 31 20° to -25°, under nitrogen, was added 12.3 ml of dimethylsulfide (10.4 g, 0.167 mol) with stirring. The mixture was stirred for 30 min, then the dienol VI (20 g, 0.0839 mol) in 50 ml of toluene was added gradually over a period of 20 min at -20° to -25°. The mixture was held at -20° for about 20 min, warmed briefly to -5°, then cooled rapidly to -50° and 23.5 ml of triethylamine was added with vigorous stirring. The mixture was warmed to -15° and then to 0°, and after about 10 min 75 ml of water was added. The organic phase was separated, washed with 1 N sulfuric acid, water, dilute sodium bicarbonate and brine, dried over sodium sulfate, and solvent evaporated. The product was chromatographed on 40 g Woelm silica using 10% ether in hexane. The crude aldehyde was crystallized twice from hexane at -50° to yield (11Z,13Z)-11,13-hexadecadien-1-al, m.p. 7°-8°.

Aufarbeitung

  1. temperaturecooled to 31 20° to -25°, under nitrogen
  2. stirringThe mixture was stirred for 30 min
  3. temperaturewarmed briefly to -5°
  4. temperaturecooled rapidly to -50°
  5. temperatureThe mixture was warmed to -15°
  6. customThe organic phase was separated
  7. washwashed with 1 N sulfuric acid, water, dilute sodium bicarbonate and brine
  8. dry with materialdried over sodium sulfate, and solvent
  9. customevaporated
  10. customThe product was chromatographed on 40 g Woelm silica using 10% ether in hexane
  11. customThe crude aldehyde was crystallized twice from hexane at -50°

Quellen und Nachweise

ORD-Eintrag
ord-b58ef982844a43a0877cb7ed363c53f6
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04198533

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