Hydrochloric Acid → 2-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

HRID 126734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 126734
Cl[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)=[O:3].[O:16]1CCOC[CH2:17]1.Cl>[Cl-].[Na+].O>[OH:16][CH2:17][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 202875962-[6-(Chloroformyl)hexyl]cyclopent-2-en-1-one

Produkt 1

HCID 202876282-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6.3 g. of 2-[6-(chloroformyl)hexyl]-cyclopent-2-en-1-one (Example 75) and 16 g. of tris-trimethylsilyloxyethylene (Example 74) are stirred at 90° to 100° C. under argon for one hour. To this mixture is added 25 ml. of dioxane and 10 ml. of 0.6N hydrochloric acid. The mixture is heated at 80° C. for 30 minutes. The mixture is poured into brine and extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed and the residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid to give 1.7 g. of the title compound (Rf =0.45).

Aufarbeitung

  1. additionA mixture of 6.3 g
  2. additionTo this mixture is added 25 ml
  3. extractionextracted with ether
  4. washThe ether solution is washed with saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed
  7. customthe residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid
  8. customto give 1.7 g

Quellen und Nachweise

ORD-Eintrag
ord-e6d99089f33c41beb69c201e5abb07da
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254036

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