Hexane → 1-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene

HRID 1975614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975614
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][O:10][CH3:11])C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1.CCCCCC>COC(C)(C)C.O1CCCC1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=[CH:9][O:10][CH3:11])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 100835924-(4-Bromophenyl)cyclohexanone

Produkt 1

HCID 190979141-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzeneAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

20.4 g of triphenyl-methoxymethyl-phosphonium chloride were suspended in 60 ml of t-butyl methyl ether while gassing with argon in a sulphonation flask having a thermometer, mechanical stirrer, dropping funnel and solid substance addition tube and treated at -10° C. within 10 minutes with 6.6 g of solid potassium t-butylate. After completion of the addition the mixture was stirred at -10° C. to 0° C. for 30 minutes, then the deep orange, heterogeneous reaction mixture was treated dropwise at 0° C. with a solution of 10 g of 4-(4-bromophenyl)cyclohexanone in 50 ml of absolute tetrahydrofuran, subsequently stirred at room temperature for 24 hours, poured into 500 ml of hexane and filtered. Low-pressure chromatography of the concentrated residue (13.9 g) on silica gel with hexane/ethyl acetate (vol. 9:1) gave 10.4 g of 1-bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene as a colourless oil.

Aufarbeitung

  1. customwhile gassing with argon in a sulphonation flask
  2. additionfunnel and solid substance addition tube
  3. additionAfter completion of the addition the mixture
  4. stirringsubsequently stirred at room temperature for 24 hours
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c7d89244b33a41298f701f20d983df87
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288428

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