Hydrochloric Acid → 2,7-Didocosyloxy-9-fluorenone

HRID 1047393

Reaktionsgleichung

Reaktionsgleichung von HRID 1047393
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].Cl>CN(C=O)C>[CH2:23]([O:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 813551-Bromodocosane2×HCID 43541812,7-Dihydroxyfluoren-9-one

Produkt 1

HCID 667190952,7-Didocosyloxy-9-fluorenoneAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,7-Dihydroxy-9-fluorenone (1 g, 4.71 mmol) was dissolved in DMF (40 ml), and potassium carbonate (1.95 g, 14.1 mmol) and docosyl bromide (96%, 4.02 g, 9.91 mmol) were added. The mixture was stirred overnight at 80° C., docosyl bromide (0.40 g, 0.99 mmol) was further added and the mixture was stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, 1N hydrochloric acid (120 ml) was added thereto in a water bath to allow precipitation. The crystals were collected by filtration and slurry washed once with 1N hydrochloric acid (40 ml), once with pure water (40 ml) and once with methanol (40 ml) to give 2,7-didocosyloxy-9-fluorenone (4.20 g, docosyl bromide mixture).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customin a water bath to allow
  5. customprecipitation
  6. filtrationThe crystals were collected by filtration and slurry
  7. washwashed once with 1N hydrochloric acid (40 ml), once with pure water (40 ml) and once with methanol (40 ml)

Quellen und Nachweise

ORD-Eintrag
ord-a6db3e8cc7ca4091b3cfe0b06f9bf1da
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569453B2

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