Potassium Hydroxide → (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

HRID 1701238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1701238
[OH:1][CH2:2][C@H:3]([CH3:16])[CH2:4][C:5](=O)[CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].[OH-].[K+].O.NN>C(O)COCCO>[CH3:16][C@H:3]([CH2:4][CH2:5][CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:2][OH:1]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11042498(2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one

Produkt 1

HCID 10353213(2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Versuchsvorschrift

A mixture of 3.98 g. (0.0174 mole) of (2R,6R)-1-hydroxy-2,6,10-trimethylundecan-4-one, 108 ml. of diethylene glycol, 25 g. of KOH and 43.5 ml. of hydrazine hydrate was stirred and heated until distillation began. Distillation was then continued until the internal temperature of the reaction mixture reached 195° C. then the mixture was maintained at reflux for 4 hours. After cooling, the resulting mixture was treated with ice and 3 N aqueous HCl and worked-up by ether extraction in the manner of Example 1 giving 2.9 g. of a pale yellow oil. This material was chromatographed on 180 g. of silica gel. Elution with 4:1 parts by volume hexane-ether yielded (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol which was evaporatively distilled affording 2.22 g. of a colorless oil, b.p. 90°-105° C. (bath temperature) (0.2 mm Hg.); [α]25D+9.44° (c 2.04, hexane).

Aufarbeitung

  1. additionA mixture of 3.98 g
  2. temperatureheated until distillation
  3. distillationDistillation
  4. customreached 195° C.
  5. temperaturethe mixture was maintained
  6. temperatureat reflux for 4 hours
  7. temperatureAfter cooling
  8. additionthe resulting mixture was treated with ice and 3 N aqueous HCl
  9. extractionworked-up by ether extraction in the manner of Example 1 giving 2.9 g
  10. customThis material was chromatographed on 180 g
  11. washElution with 4:1 parts by volume hexane-ether

Quellen und Nachweise

ORD-Eintrag
ord-f8c090d68050442798eac25931cd5971
Quelldatensatz
uspto-grants-1980_03
Patentnummer
US04191842

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