Sodium → 10,11-Epoxy-3,7,10,11-tetramethyl-2,6-dodecadienoic acid ethyl ester

HRID 1658043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1658043
[O:1]1[C:13]([CH3:15])([CH3:14])[C:2]1([CH3:16])[CH2:3][CH2:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8]C(=O)C.[CH2:17]([O:19][C:20](=[O:30])[C:21]([CH2:28][CH3:29])(CC)P(O)(O)=O)[CH3:18].[Na]>C(O)C>[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[C:28]([CH3:29])[CH2:8][CH2:7][CH:6]=[C:5]([CH3:12])[CH2:4][CH2:3][C:2]1([CH3:16])[O:1][C:13]1([CH3:15])[CH3:14])[CH3:18]

Komponenten

5

Edukt 3

HCID 5360545SodiumHCID 17846631Ethyl diethyl-phosphonoacetateHCID 541284819,10-Epoxy-6,9,10-trimethyl-undec-5-en-2-one

Produkt 1

HCID 5374754010,11-Epoxy-3,7,10,11-tetramethyl-2,6-dodecadienoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of 25 g. of 9,10-epoxy-6,9,10-trimethyl-undec-5-en-2-one and 24.8 g. of diethyl phosphonoacetic acid ethyl ester in 160 ml. of absolute ethanol, there was added dropwise while cooling with ice, a solution containing 2.56 g. of sodium in 65 ml. of absolute ethyl alcohol. The mixture was allowed to stand for 14 hours at room temperature and evaporated subsequently under vacuum. The residue was poured into a standard aqueous sodium chloride solution, exhaustively extracted with diethyl ether, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. Fractional distillation at high vacuum gave 10,11-epoxy-3,7,10,11-tetramethyl-2,6-dodecadienoic acid ethyl ester; b.p. 110°-113°C./0.01 mmHg; nD20 = 1.4792.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. additiona solution containing 2.56 g
  3. customevaporated subsequently under vacuum
  4. additionThe residue was poured into a standard aqueous sodium chloride solution
  5. extractionexhaustively extracted with diethyl ether
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. distillationFractional distillation at high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-211de8d244c5499ea039c74bffd02fca
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03962428

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