Ethyl Bromide → 7-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

HRID 26177

Reaktionsgleichung

Reaktionsgleichung von HRID 26177
C(Br)C.[Mg].[OH:5][C:6]([CH3:16])([CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14])[C:7]#[CH:8].[CH3:17][C:18]1([CH3:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[C:19]1=[O:25].[Cl-].[NH4+]>C(OCC)C.C1C=CC=CC=1>[OH:5][C:6]([CH3:16])([C:7]#[C:8][C:19]1([OH:25])[CH:20]([CH3:24])[CH2:21][CH2:22][CH2:23][C:18]1([CH3:26])[CH3:17])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14]

Komponenten

8

Edukt 5

HCID 6332Ethyl BromideHCID 170002,2,6-TrimethylcyclohexanoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 542483613,7-Dimethylnona-4,6,8-trien-1-yn-3-ol

Produkt 1

HCID 543180627-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of ethyl bromide (1.75 g.) in diethyl ether was added to a suspension of magnesium (0.385 g.) in ether and the mixture was heated to reflux for 30 minutes. A solution of the alcohol, 3-hydroxy-3,7-dimethyl-nona-4,6,8-trien-1-yne, (1.0 g.) in dry benzene was added and the mixture refluxed 30 minutes. A solution of 2,2,6-trimethylcyclohexanone (1.12 g.) in benzene was added and the mixture refluxed for 15 minutes and poured into saturated aqueous ammonium chloride solution. The organic phase was washed with brine dried and concentrated to give 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne which was chromatographed on activity III alumina to give pure 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethyl-cyclohexyl)-nona-1,3,5-trien-8-yne.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture refluxed 30 minutes
  4. temperaturethe mixture refluxed for 15 minutes
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-35cc3eed3fdd4c9c830572cf9db82737
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148829

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