Hydrochloric Acid → 2-Docosyloxy-9-fluorenone

HRID 573025

Reaktionsgleichung

Reaktionsgleichung von HRID 573025
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH2:23][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][CH3:43].Cl>CN(C=O)C>[CH2:43]([O:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1)[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][CH2:23][CH3:22]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 813551-BromodocosaneHCID 813862-Hydroxyfluoren-9-one

Produkt 1

HCID 667190052-Docosyloxy-9-fluorenoneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Hydroxy-9-fluorenone (196 mg, 2.04 mmol) was dissolved in DMF (8 ml), potassium carbonate (423 mg, 3.06 mmol), and docosyl bromide (96%, 785 mg, 1.93 mmol) were added. The mixture was heated to 80° C. and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid (4 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (23 ml), and washed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml). The solvent of the organic layer was evaporated, and the residue was precipitated with methanol (10 ml) to give 2-docosyloxy-9-fluorenone (934 mg, 1.85 mmol, 96%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customin a water bath to quench
  4. customthe reaction
  5. extractionThe mixture was extracted with chloroform (23 ml)
  6. washwashed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml)
  7. customThe solvent of the organic layer was evaporated
  8. customthe residue was precipitated with methanol (10 ml)

Quellen und Nachweise

ORD-Eintrag
ord-c11d3c4b780746668eb5623590f78cb2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029504B2

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