1,2-Dichloroethane → 4-(1,4-Dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)-cyclohexene

HRID 1419655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419655
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)(O)[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.ClCCCl>C(O)CO>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=4)=[CH:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 111,2-DichloroethaneHCID 699629074-(1,4-Dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)cyclohexanol

Produkt 1

HCID 699658034-(1,4-Dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)-cyclohexeneAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

A mixture of 174.3 g of 4-(1,4-dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)cyclohexanol, 1000 ml of 1,2-dichloroethane, 25 ml of ethylene glycol and 25 g of Amberlyst 15 was boiled under reflux for 22 hrs., the condensate being dried over a dropping funnel filled with 175 g of neutral aluminiumoxide. Then, the reaction mixture was cooled, filtered, washed with water and the organic phase was dried over sodium sulphate. Subsequent chromatography on 1000 g of silica gel with hexane/ethyl acetate (90:1) gave 124.2 g of 4-(1,4-dioxaspiro[4,5]dec-8-yl)-1-(3-fluorophenyl)-cyclohexene as colorless crystals. M.p. of a sample recrystallized from methylene chloride/hexane: 133.7°-135.3° C.

Aufarbeitung

  1. temperatureunder reflux for 22 hrs
  2. custom, the condensate being dried over a dropping funnel
  3. additionfilled with 175 g of neutral aluminiumoxide
  4. temperatureThen, the reaction mixture was cooled
  5. filtrationfiltered
  6. washwashed with water
  7. dry with materialthe organic phase was dried over sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-9ea318dab5a142aab782395aac078a0c
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05888423

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