1-Pentyne → 1-Chlorooct-4-yn-3-ol

HRID 66992

Reaktionsgleichung

Reaktionsgleichung von HRID 66992
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH3:10].[Cl:11][CH2:12][CH2:13][CH:14]=[O:15].[Cl-].[NH4+]>CCCCCC>[Cl:11][CH2:12][CH2:13][CH:14]([OH:15])[C:6]#[C:7][CH2:8][CH2:9][CH3:10]

Komponenten

6

Edukt 4

HCID 123091-PentyneHCID 25517Ammonium ChlorideHCID 29596Propanal, 3-chloro-HCID 178418339Butyllithium

Produkt 1

HCID 204655481-Chlorooct-4-yn-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

To 68 ml. of 1.6 M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55μ (--C≡C--); vapor phase chromatography shows one peak.

Aufarbeitung

  1. additionThe resulting white sludge is diluted with 20 ml
  2. custombrought to 10° C.
  3. additiontreated with 11 g
  4. stirringto stir at ambient temperature for 18 hours
  5. customThe organic phase is separated
  6. washwashed
  7. additionwith dilute hydrochloric solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. distillationDistillation
  10. customgives 5.1 g

Quellen und Nachweise

ORD-Eintrag
ord-468d1b6d25904b579ad5f074478fc524
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343949

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