beta-Cyclocitral → HCID 53646445, Verbindung

HRID 903290

Reaktionsgleichung

Reaktionsgleichung von HRID 903290
Br[CH:2]=[CH:3][CH3:4].[Mg].[CH3:6][C:7]1[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[C:8]=1[CH:15]=[O:16].[NH4+].[Cl-]>O1CCCC1>[CH3:6][C:7]1[CH2:12][CH2:11][CH2:10][C:9]([CH3:13])([CH3:14])[C:8]=1[CH:15]([OH:16])[CH:2]=[CH:3][CH3:4]

Komponenten

6

Edukt 4

HCID 9895beta-CyclocitralHCID 115331-Bromo-1-propene2×HCID 25517Ammonium ChlorideHCID 5462224Magnesium

Produkt 1

HCID 53646445HCID 53646445, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

In an atmosphere of nitrogen, a solution of 280 g. of 1-bromopropene in 430 ml. of tetrahydrofuran was added dropwise at 63°-65° into a suspension of 53.3 g. of magnesium turnings in 660 ml. of tetrahydrofuran. During the addition the reflux condenser fitting the reaction vessel was cooled to -40° to -50° in order to prevent escaping of the vapours of unreacted 1-bromopropene. The mixture was stirred for an additional 21/2 hours at 60°-62° after which it was cooled to 0°. A solution of 278 g. of β-cyclocitral in 350 ml. of tetrahydrofuran was then added dropwise between 0° and 7°. The mixture was allowed to stand overnight then it was poured onto a mixture of ice and saturated aqueous NH4Cl solution. The organic layer was removed and the aqueous phase extracted with petroleum-ether (b.p. 30°-50°). The combined extracts were washed as usual, dried and then evaporated under vacuum. The residue gave 350 g. of crude 2,6,6-trimethyl-1-[1-hydroxy-2-butenyl]-1-cyclohexene which was used without further purification.

Aufarbeitung

  1. additionDuring the addition the reflux condenser
  2. temperaturewas cooled to -40° to -50° in order
  3. temperaturewas cooled to 0°
  4. waitto stand overnight
  5. customThe organic layer was removed
  6. extractionthe aqueous phase extracted with petroleum-ether (b.p. 30°-50°)
  7. washThe combined extracts were washed as usual,
  8. customdried
  9. customevaporated under vacuum
  10. customThe residue gave 350 g
  11. customof crude 2,6,6-trimethyl-1-[1-hydroxy-2-butenyl]-1-cyclohexene which was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ab396a25787c4210bddfbb1dc4016a7e
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04226892

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